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[ CAS No. 129488-10-4 ] {[proInfo.proName]}

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Chemical Structure| 129488-10-4
Chemical Structure| 129488-10-4
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Quality Control of [ 129488-10-4 ]

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Product Details of [ 129488-10-4 ]

CAS No. :129488-10-4 MDL No. :MFCD04114656
Formula : C12H15N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LRSDPIIWOZRHNJ-UHFFFAOYSA-N
M.W : 233.27 Pubchem ID :19800556
Synonyms :

Calculated chemistry of [ 129488-10-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 66.34
TPSA : 70.14 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.41
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 1.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.84
Solubility : 0.337 mg/ml ; 0.00144 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.127 mg/ml ; 0.000543 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.63
Solubility : 0.542 mg/ml ; 0.00232 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.36

Safety of [ 129488-10-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 129488-10-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 129488-10-4 ]

[ 129488-10-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 129488-09-1 ]
  • [ 129488-10-4 ]
YieldReaction ConditionsOperation in experiment
100% In methanol; palladium; ethyl acetate; Part B Preparation of 5-amino-indazole-1-carboxylic acid t-butyl ester In a Paar flask charged with palladium (10 wt percent on carbon, 0.44 g) was added ethyl acetate (30 mL) and 5-nitro-indazole-1-carboxylic acid t-butyl ester (1.61 g, 6.2 mmol). The reaction mixture was hydrogenated at 50 psi for 30 minutes with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of methanol and the combined filtrates were concentrated in vacuo to give a white solid (1.4 g, 100percent). 1H NMR (300 MHz, CDCl3), delta: 7.99 (s, 1H), 7.97 (d, J=10, 1H), 6.94 (dd, J=10, J'=2, 1H), 6.92 (d, J=2, 1H), 1.71 (s, 9H).
98.6% With palladium 10% on activated carbon; hydrogen; In methanol; Compound Reg-1-1-b (38 g, 144.35 mmol) was dissolved in methanol (700 mL), Pd/C (3.8 g, 10percent water) wasadded, purge with hydrogen was performed for three times, and the reaction was performed under a hydrogen atmosphereovernight. Thin layer chromatography (petroleum ether : ethyl acetate=3:1) indicated the reaction was complete. Thereaction solution was filtered through Celite to afford compound Reg-1-1-c (33.2 g, brown solid, yield: 98.6percent).1H NMR (400 MHz, CDCl3) delta 7.97 (d, J = 10.8 Hz, 2H), 7.00 - 6.87 (m, 2H), 3.74 (s, 2H), 1.71 (s, 9H).
98.6% With palladium on activated charcoal; hydrogen; In methanol; water; Compound Reg-1-1-b (38 g, 144.35 mmol) was dissolved in methanol (700 mL), Pd/C (3.8 g, 10percent water) was added, purge with hydrogen was performed for three times, and the reaction was performed under a hydrogen atmosphere overnight. Thin layer chromatography (petroleum ether : ethyl acetate=3:1) indicated the reaction was complete. The reaction solution was filtered through Celite to afford compound Reg-1-1-c (33.2 g, brown solid, yield: 98.6percent). 1H NMR (400 MHz, CDCl3) delta 7.97 (d, J = 10.8 Hz, 2H), 7.00 - 6.87 (m, 2H), 3.74 (s, 2H), 1.71 (s, 9H).
With hydrogen;palladium on activated charcoal; In tetrahydrofuran; at 40℃; under 2585.81 Torr; for 16h; To a solution of 5-nitro-indazole-1 -carboxylic acid tert-butyl ester (300 g, 1 .1 mol, 1 .0 eq) in THF (3 L), and the mixture was hydrogenated at 40 °C with Pd/C (30 g) as catalyst in the presence of H2 (50 psi). The reaction mixture was stirred at 40 °C fori 6 hrs. TLC (PE: EA=4:1 ) showed the reaction was complete. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1 -carboxylic acid tert-butyl ester (252 g, 95percent) which was used directly for next step without purification.
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 40℃; under 2585.81 Torr; for 16h; To a solution of 5-nitro-indazole-1-carboxylic acid tert-butyl ester (300 g, 1.1 mol, 1.0 eq) in THF (3 L), and the mixture was hydrogenated at 40° C. with Pd/C (30 g) as catalyst in the presence of H2 (50 psi). The reaction mixture was stirred at 40° C. for 16 hrs. TLC (PE:EA=4:1) showed the reaction was complete. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1-carboxylic acid tert-butyl ester (252 g, 95percent) which was used directly for next step without purification.
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 40℃; under 2585.81 Torr; for 16h; To a solution of 5-nitro-indazole-1-carboxylic acid tert-butyl ester (300 g, 1.1 mol, 1.0 eq) in THF (3 L) was added Pd/C (30 g). The reaction mixture was stirred at 40°C for 16 hours under pressure of H2 (50 psi). TLC (PE: EtOAc = 4:1) showed complete conversion. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1-carboxylic acid tert-butyl ester (252 g, 95percent) which was used directly for next step without purification.
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; for 3h; [0003711 To a stirred solution of compound 2 (1 g, 1 eq) in ethyl acetate (30 mL), 10percentPd-C (0.28 g) was added under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 h under hydrogen atmosphere (balloon pressure). The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated under reduced pressure to afford the title compound 3.

  • 2
  • [ 129488-10-4 ]
  • [ 911418-02-5 ]
  • [ 911418-03-6 ]
YieldReaction ConditionsOperation in experiment
59% In isopropyl alcohol; at 95℃; for 5h; A mixture of 4-chloro-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-6- yl acetate (3.14g, 7.42 mmol) and tert-butyl 5-amino-lH-indazole-l-carboxylate (1.85g, 7.93 mmol) in IPA (180 mL) was heated at 95 0C for 5 h. The mixture was allowed to cool to RT and the solid was collected via filtration. The solid was subjected to flash chromatography (SiO2, CH2Cl2/Me0H) to give the desired compound tert-butyl 5-(6- acetoxy-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-4-ylamino)- 1 H-indazole- 1 - carboxylate (2.7Og, 4.36 mmol, 59percent). MS 620.4 (M+l). HPLC retention time 8.10 mins (5-95-13 method).
59% In isopropyl alcohol; at 95℃; for 5h; A mixture of 4-chloro-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-6- yl acetate (3.14g, 7.42 mmol) and /<;?/v-butyl 5-amino- I H-indazole- l -carboxylate (1.85g, 7.93 mmol) in IPA (180 mL) was heated at 95 °C for 5 h. The mixture was allowed to cool to RT and the solid was collected via filtration. The solid was subjected to flash chromatography (SiOi, C^Ch/MeOH) to give the desired compound /ctau/-butyl 5-(6- acetoxy-2-(3-fluoro-4-(phenyl)phenyI)-7-methoxyquinazolin-4-ylamino)- lH-indazole- l - carboxylate (2.7Og, 4.36 mmol, 59percent). MS 620.4 (M+ 1 ). HPLC retention time 8. 10 mi ns (5-95- 13 method).
59% In isopropyl alcohol; at 95℃; for 5h; [0275] A mixture of 4-chloro-2~(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolm-6-yl acetate (3.14g, 7.42 mmol) and tert-huty\\ 5-amino-lH-indazole-l-carboxylate (1.85g, 7.93 mmol) in IPA (180 mL) was heated at 95 °C for 5 h. The mixture was allowed to cool to RT and the solid was collected via filtration. The solid was subjected to flash chromatography (SiO2, CH2Cl2MeOH) to give the desired compound tert-butyl 5-(6- acetoxy-2-(3-fluoro-4-(phenyl)phenyl)-7-methoxyquinazolin-4-ylamino)-lH-indazole-l- carboxylate (2.7Og, 4.36 mmol, 59percent). MS 620.4 (M+l). HPLC retention time 8.10 mins (5-95-13 method).
  • 3
  • [ 129488-10-4 ]
  • [ 911417-24-8 ]
  • [ 911417-25-9 ]
YieldReaction ConditionsOperation in experiment
98% In isopropyl alcohol; at 95℃; for 0.25h; 3-(4-Chloroquinazolin-2-yl)phenyl acetate (9.77 g, 29.97mmole) was dissolved in isopropanol (290 mL) and tert-butyl 5-amino-lH-indazole-l-carboxylate (6.99 g, 29.97 mmole) was added. The solution was heated to 95 0C and stirred for 0.25 h. A gelatinous formation developed which was manually broken up and dissolution gradually occurred followed by formation of a yellow precipitate. The reaction was stirred for an additional EPO <DP n="108"/>0.25 h, cooled to ambient temperature and filtered. The filtered solid was washed with ether and then dried under high vacuum overnight to give tert-butyl 5-(2-(3- acetoxyphenyl)quinazolin-4-ylamino)-lH-indazole-l-carboxylate. (14.58 g, mmol, 98 percent)
98% In isopropyl alcohol; at 95℃; for 0.5h; 3-(4-ChIoroquinazolin-2-yl)phenyl acetate (9.77 g, 29.97mmole) was dissolved in isopropanol (290 mL) and /m-butyl 5-amino- I H-indazole-l -carboxylate (6.99 g, 29.97 mmole) was added. The solution was heated to 95 °C and stirred for 0.25 h. A gelatinous formation developed which was manually broken up and dissolution gradually occurred followed by formation of a yellow precipitate. The reaction was stirred for an additional 0.25 h, cupsilonupsilonled lupsilon ambient temperature and Tillered. The filtered solid was washed wilh ether and then dried under high vacuum overnight to give ten-butyl 5-(2-(3- acetoxyphenyl)quinazolin-4-ylamino)- I H-indazole- l -carboxylate. ( 14.58 g, mmol, 98 percent)
98% In isopropyl alcohol; at 95℃; for 0.5h; [0181] 3-(4-Chloroquinazolin-2-yl)phenyl acetate (9.77 g, 29.97mmole) was dissolved in isopropanol (290 mL) and tert-butyl 5-amino-lH-indazole-l-carboxylate (6.99 g, 29.97 mmole) was added. The solution was heated to 95 0C and stirred for 0.25 h. A gelatinous formation developed which was manually broken up and dissolution gradually occurred followed by formation of a yellow precipitate. The reaction was stirred for an additional 0.25 h, cooled to ambient temperature and filtered. The filtered solid was washed with ether and then dried under high vacuum overnight to give tert-butyl 5-(2-(3- acetoxyphenyl)quinazolin-4-ylamino)-lH-indazole-l-carboxylate. (14.58 g, mmol, 98 percent)
  • 4
  • [ 129488-10-4 ]
  • [ 911418-13-8 ]
  • [ 911418-14-9 ]
YieldReaction ConditionsOperation in experiment
77% In isopropyl alcohol; at 95℃; for 2h; A mixture of 4-chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate (4.0Og, 9.88 mmole), tert-butyl 5-amino-lH-indazole-l-carboxylate (2.42g, 10.37 mmole) in wo-propanol (130 mL) was stirred at 95 0C for 2 h. The reaction was cooled to RT and the crude product was filtered and then washed with ether, wo-propanol, and hexane and dried under vacuum to give tert-butyl 5-(6-acetoxy-2-[(3-phenyl)phenyl)-7- methoxyquinazolin-4-ylamino)-lH-indazole-l-carboxylate ( 4.33g, 7.20 mmole, 77percent over two steps). MS 602 (M+ 1). HPLC retention time 6.47 mins.
In isopropyl alcohol; at 95℃; for 2h; A mixture of 4-chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate (4.0Og, 9.88 mmole), te/7-butyl 5-amino- I H-indazole-l -carboxylate (2.42g, 10.37 mmole) in /.vo-propanol ( 130 mL) was stirred at 95 °C for 2 h The reaction was cooled to RT and the crude product was filtered and then washed with ether, lambdavo-propanol, and hexane and dried under vacuum to give /c/7-butyl 5-(6-acetoxy-2-[(3-phenyl)phenyl)-7- methoxyquinazolin-4-yIamino)- l H-indazole- l-carboxylate ( 4.33g, 7.20 mmole, 77percent over two steps). MS 602 (M+ 1 ). HPLC retention time 6.47 mins.
In isopropyl alcohol; at 95℃; for 2h; [0286] A mixture of 4-chloro-2-[(3-phenyl)phenyl]-7-methoxyquinazolin-6-yl acetate (4.0Og, 9.88 mmole), tert-butyl 5-amino-lH-mdazole-l-carboxylate (2.42g, 10.37 mmole) in zso-propanol (130 mL) was stirred at 95 0C for 2 h. The reaction was cooled to RT and the crude product was filtered and then washed with ether, wo-propanol, and hexane and dried under vacuum to give tert-hvXyl 5-(6-acetoxy-2-[(3-phenyl)phenyl)-7- methoxyquinazolin-4-ylamino)-lH-indazole-l-carboxylate ( 4.33g, 7.20 mmole, 77percent over two steps). MS 602 (M+ 1). HPLC retention time 6.47 mins.
  • 5
  • [ 129488-10-4 ]
  • [ 911418-32-1 ]
  • [ 911418-33-2 ]
YieldReaction ConditionsOperation in experiment
84% In isopropyl alcohol; at 95℃; for 5h; A mixture of 4-chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate (1.63g, 4.74 mmol) and tert-butyl 5-amino-lH-indazole-l-carboxylate (1.16g, 4.28 mmol) in IPA (80 mL) were heated at 95 0C for 5h. The mixture was allowed to cool to RT, the yellow solid was collected via filtration and washed with Et2O to give the product tert-butyl 5-(6- EPO <DP n="177"/>acetoxy-2-(3-nitrophenyl)quinazolin-4-ylamino)- 1 H-indazole- 1 -carboxylate (2.14g, 3.96mmol, 84percent). HPLC retention time 9.649 min.
84% In isopropyl alcohol; at 95℃; for 5h; [0309] A mixture of 4-chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate (1.63g, 4.74 mmol) and fert-butyl 5-amino-lH-indazole-l-carboxylate (1.16g, 4.28 mmol) in IPA (80 niL) were heated at 95 °C for 5h. The mixture was allowed to cool to RT, the yellow solid was collected via filtration and washed with Et2O to give the product tert-butyl 5-(6- acetoxy-2-(3-nitrophenyl)quinazolin-4-ylamino)-lH-indazole-l-carboxylate (2.14g, 3.96mmol, 84percent). HPLC retention time 9.649 min.
In isopropyl alcohol; at 95℃; for 5h; A mixture of 4-chloro-2-(3-nitrophenyl)quinazolin-6-yl acetate ( 1 63g, 4 74 mmol) and /tw -butyl 5-amino-l H-indazole- l -carboxylate ( I 16g, 4 28 mmol) in IPA (80 mL) were heated at 95 °C for 5h. The mixture was allowed to cool to RT, the yellow solid was collected via filtration and washed with Et2O to give the product tert-buty] 5-(6- acetoxy-2-(3-nitrophenyl)quina2psilin-4-ylamino)- 1H-indazole-1-carboxylate (2.14g, 3.96mmol, 84percent). KPLC retention time 9.649 min.
  • 6
  • [ 129488-10-4 ]
  • [ 911418-47-8 ]
  • [ 911418-48-9 ]
YieldReaction ConditionsOperation in experiment
100% In isopropyl alcohol; for 5h;Heating / reflux; A mixture of 4-chloro-7-methoxy-2-(3-nitrophenyl)quinazolin-6-yl acetate (1.6Og, 4.23 mmol) and tert-butyl 5-amino-lH-indazole-l-carboxylate (1.Og, 4.28 mmol) were refluxed in anhydrous wo-propanol (6OmL) for 5 h. The mixture was allowed to cool to RT, upon which the solid was collected via filtration and was washed with Et2O to give EPO <DP n="188"/>tert-butyl 5-(6-acetoxy-7-methoxy-2-(3-nitrophenyl)quinazolin-4-ylamino)- 1 H-indazole- 1-carboxylate. (2.2g, 4.23mmol, 100percent). HPLC retention time = 7.75 mins.
100% In isopropyl alcohol; for 5h;Reflux; A mixture of 4-chloro-7-methoxy-2-(3-nitrophenyl)quinazolin-6-yl acetate (1 6Og, 4.23 mmol) and lerl-buty\\ 5-amino-1H-indazole- l -carboxylate ( 1 Og, 4 28 mmol) were refluxed in anhydrous /.so-propanol (6OmL) for 5 h The mixture was allowed to cool to RT, upon which the solid was collected via filtration and was washed with EtaO to give /etau/-butyl 5-(6-acetoxy-7-methoxy-2-(3-nitrophenyl)quinazolin-4-ylamino)-l H-indazole- 1 -carboxylate (2 2g, 4 23mmol, 100percent) HPLC retention time = 7 75 mins
100% In isopropyl alcohol; for 5h;Heating / reflux; [0336] A mixture of 4-chloro-7-methoxy-2-(3-nitrophenyl)quinazolin-6-yl acetate(1.6Og, 4.23 mmol) and tert-buty\\ 5-amino-lH-indazole-l-carboxylate (l.Og, 4.28 mmol) were refluxed in anhydrous wo-propanol (6OmL) for 5 h. The mixture was allowed to cool to RT, upon which the solid was collected via filtration and was washed with Et2O to give tert-butyl 5-(6-acetoxy-7-methoxy-2-(3-nitrophenyl)quinazolin-4-ylamino)-lH-mdazole- 1-carboxylate. (2.2g, 4.23mmol, 100percent). HPLC retention time = 7.75 mins.
  • 7
  • [ 129488-10-4 ]
  • [ 93256-31-6 ]
  • [ 911417-27-1 ]
YieldReaction ConditionsOperation in experiment
79% In isopropyl alcohol; at 95℃; for 1.5h; A suspension of 4-chloro-2-(3-nitrophenyl)quinazoline (6.3 g, 21.9 mmole), 5-amino-lH-indazole-l-carboxylate (5.10 g, 21.9 mmole) in isopropanol (300 mL) was heated at 95 0C for 1.5 h. The suspension was filtered and the filtered solid was washed with isopropanol. The product was dried under high vacuum for several hours to give the desired product tert-butyl 5-(2-(3-nitrophenyl)quinazolin-4-ylamino)-lH- indazole-1-carboxylate. ( 8.3 g, mmol, 79percent).
79% In isopropyl alcohol; at 95℃; for 1.5h; A suspension of 4-chIoro-2-(3-nitrophenyl)quinazoline (6.3 g, 21.9 mmole), /e/7-butyl 5-amino-l H-indazole-1-carboxylate (5.10 g, 21.9 mmole) in isopropanol (300 mL) was heated at 95 °C for 1.5 h. The suspension was filtered and the filtered solid was washed with isopropanol. The product was dried under high vacuum for several hours to give the desired product teriota-buty\\ 5-(2-(3-nitrophenyl)quinazolin-4-ylamino)- 1H- indazole-1 -carboxylate. ( 8.3 g, mmol, 79percent).
79% In isopropyl alcohol; at 95℃; for 1.5h; [0186] A suspension of 4-chloro-2-(3-nitrophenyl)quinazoline (6.3 g, 21.9 mmole), tert-butyl 5-amino-lH-indazole-l-carboxylate (5.10 g, 21.9 mmole) in isopropanol (300 mL) was heated at 95 0C for 1.5 h. The suspension was filtered and the filtered solid was washed with isopropanol. The product was dried under high vacuum for several hours to give the desired product tert-butyl 5-(2-(3-nitrophenyl)quinazolin-4- ylamino)-lH-indazole-l-carboxylate. ( 8.3 g, mmol, 79percent).
  • 8
  • [ 129488-10-4 ]
  • [ 911418-78-5 ]
  • [ 911418-79-6 ]
YieldReaction ConditionsOperation in experiment
71% In isopropyl alcohol; at 95℃; for 8.5h; A mixture of 4-chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3 - nitrophenyl)quinazoline (0.500g,1.28 mmol) and 5-amino-lH-indazole-l-carboxylate (0.314g, 1.34mmol) in iso-propanol (30 mL) was heated at 95°C for 30 minutes and at 95 0C for 8 h. The mixture was allowed to cool to RT and the solid was collected via filtration. The cake was washed with iso-propanol and Et2O, triturated with CH2Cl2 and EtOAc and dried in vacuo to give tert-Butyl 5-(7-methoxy-6-(2-methoxyethoxy)-2-(3- nitrophenyl)quinazolin-4-ylamino)-lH-indazole-l-carboxylate (0.56Og, 0.955 mmol, 71percent). MS 587 (M+l). HPLC retention time 7.21 mins.
71% In isopropyl alcohol; at 95℃; for 8.5h; A mixture of 4-chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3- nitrophenyl)quinazoline (0 500g,1.28 mmol) and 5-amino-l H-indazole-l -carboxylate (0.3 14g, 1.34mmol) in iso-propanol (30 mL) was heated at 95°C for 30 minutes and at 95 °C for 8 h The mixture was allowed to cool to RT and the solid was collected via filtration. The cake was washed with iso-propanol and Et2O, triturated with CH2Ch and EtOAc and dried in vacuo to give (erl-Buty\\ 5-(7-methoxy-6-(2-methoxyethoxy)-2-(3- nitrophenyl)quinazolin-4-ylamino)- l H-indazole-l -carboxylate (0.56Og, 0.955 mmol, 71percent). MS 587 (M+ 1 ). HPLC retention time 7.21 mins.
71% In isopropyl alcohol; at 95℃; for 8.5h; [0375] A mixture of 4-chloro-7-methoxy-6-(2-methoxyethoxy)-2-(3 - nitrophenyl)quinazoline (0.500g,1.28 mmol) and 5-amino-lH-indazole-l-carboxylate (0.314g, 1.34mmol) in iso-propanol (30 mL) was heated at 95°C for 30 minutes and at 95 0C for 8 h. The mixture was allowed to cool to RT and the solid was collected via filtration. The cake was washed with iso-propanol and Et2O, triturated with CH2Cl2 and EtOAc and dried in vacuo to give fe/t-Butyl 5-(7-methoxy-6-(2-methoxyethoxy)-2-(3- nitrophenyl)quinazolin-4-ylamino)-lH-indazole-l-carboxylate (0.560g, 0.955 mmol, 71percent). MS 587 (M+l). HPLC retention time 7.21 mins.
  • 9
  • [ 129488-10-4 ]
  • [ 911418-85-4 ]
  • [ 911418-86-5 ]
YieldReaction ConditionsOperation in experiment
100% A mixture of 2-(3-(benzyloxy)phenyl)-4-chloro-7-methoxy-6-(2- methoxyethoxy)quinazoline (1.55g, 3.44 mmol) and tert-butyl 5-amino-lH-indazole-l- carboxylate (0.842g, 3.61 mmol) in iso-propanol (100 mL) was heated at 95 0C for 2h, upon which the an additional aliquot of tert-buty\\ 5-amino-lH-indazole-l-carboxylate (0.10Og, 0.43 mmol) was added. Stirring was continued at 95 0C for a further 3 h upon which a third aliquot of tert-butyl 5-amino-lH-indazole-l-carboxylate (0.050g, 0.22 mmol) was added. Stirring was continued at 95 °C for a further 1 h upon which the mixture was allowed to cool to RT and the precipitate was collected via filtration. The solid was washed with iso-propanol and dried under vacuum to give tert-buty\\ 5-(2-(3- (benzyloxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-lH-indazole- 1-carboxylate (2.35g, 3.44 mmol, 100percent). MS 648 (M+l). HPLC retention time 7.79 mins.
100% In isopropyl alcohol; at 95℃; for 6h; A mixture of 2-(3-(benzyloxy)phenyl)-4-chloro-7-methoxy-6-(2- methoxyethoxy)quinazoline ( 1.55g, 3.44 mmol) and /e/7-butyl 5-amino- l H-indazole-1- carboxylate (0.842g, 3.61 mmol) in iso-propanol (100 mL) was heated at 95 °C for 2h, upon which the an additional aliquot of /<;?/7-butyl 5-amino-l H-indazole-l -carboxylate (0.10Og, 0.43 mmol) was added. Stirring was continued at 95 °C for a further 3 h upon which a third aliquot of /e/7-butyl 5-amino-l H-indazole- l -carboxylate (0.05Og, 0.22 mmol) was added. Stirring was continued at 95 °C for a further 1 h upon which the mixture was allowed to cool to RT and the precipitate was collected via filtration. The solid was washed with iso-propanol and dried under vacuum to give to/V-butyl 5-(2-(3- (benzyloxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)- l H-indazole- 1-carboxylate (2.35g, 3.44 mmol, 100percent). MS 648 (M+l ). HPLC retention time 7.79 mins.
100% In isopropyl alcohol; at 95℃; for 6h; [0382] A mixture of 2-(3-(benzyloxy)phenyl)-4-chloro-7-methoxy-6-(2- methoxyethoxy)quinazoline (1.55g, 3.44 mmol) and tert-butyl 5-amino-lH-indazole-l- carboxylate (0.842g, 3.61 mmol) in iso-propanol (100 mL) was heated at 95 °C for 2h, upon which the an additional aliquot of fert-butyl 5-amino-lH-indazole-l-carboxylate EPO <DP n="194"/>(0.10Og, 0.43 mmol) was added. Stirring was continued at 95 °C for a further 3 h upon which a third aliquot of tert-butyl 5-amino-lH-indazole-l-carboxylate (0.050g, 0.22 mmol) was added. Stirring was continued at 95 0C for a further 1 h upon which the mixture was allowed to cool to RT and the precipitate was collected via filtration. The solid was washed with iso-propanol and dried under vacuum to give tert-butyl 5-(2-(3- (benzyloxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-lH-indazole- 1-carboxylate (2.35g, 3.44 mmol, 100percent). MS 648 (M+l). HPLC retention time 7.79 mins.
  • 10
  • [ 24424-99-5 ]
  • [ 5401-94-5 ]
  • [ 129488-10-4 ]
YieldReaction ConditionsOperation in experiment
96% A soln of di-tert-butyl dicarbonate (6.719 g, 30.8 mmol) in DCM (20 mL) was added over 5 min to a suspension of 5-nitro-lH-indazole (5.009 g, 30.7 mmol), Et3N (4.30 mL, 30.9 mmol) and DMAP (0.751 g, 6.15 mmol) in DCM (60 mL). After 17 h the solution was washed with water (1 x 50 mL), 1 M citric acid (3 x 10 mL) and satd NaCl (1 x 20 mL), then dried (MgSO4), filtered through silica, washed with DCM and concentrated to give 7.75 g (96percent) an off-white solid. LC-MS (ESI) m/z 162 [M- Boc-H]-.
  • 11
  • [ 40114-49-6 ]
  • [ 129488-10-4 ]
  • [ 916991-31-6 ]
YieldReaction ConditionsOperation in experiment
80% With sodium tris(acetoxy)borohydride; acetic acid; In 1,1-dichloroethane; at 20℃; for 43h; To a solution of 5-amino-indazole-l-carboxylic acid tert-butyl ester (2.333 g, 10.0 mmol) and l-benzyl-piperidin-3-one (1.900 g, 10.0 mmol) in DCE (35 mL) was added NaBH(OAc)3 (95percent; 2.970 g, 13.3 mmol) followed by AcOH (0.58 mL, 10.1 mmol) at room temperature and stirring continued for 43 h. The reaction was washed with 1 M NaOH (50 mL) then the organic phase dried (MgSO4), filtered, adsorbed onto silica and purified by MPLC using gradient of 0 - 10percent /-PrOH in DCM yielding 3.24 g (80percent) of 5-(l-benzyl-piperidin-3-ylamino)-indazole-l-carboxylic acid tert-butyl ester as a brown foam. LC-MS (ESI) m/z 407 [M+H]+.
  • 12
  • [ 5401-94-5 ]
  • [ 129488-10-4 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;palladium 10% on activated carbon; In ethanol; for 23h; A suspension of 10percent Pd-C (0.054 g, 0.051 mmol in Pd) and the above carbamate Example 105 (2.647 g, 10.1 mmol) in 95percent EtOH was degassed under reduced pressure then reacted under hydrogen. After 23 h the solvent was evaporated on a rotary evaporator. EtOAc (20 mL) was added and the reaction filtered then slowly EPO <DP n="125"/>concentrated on a rotary evaporator yielding 2.335 g (100percent) of a tan solid.LC- MS (ESI) m/z 134 [M-Boc+H]+.
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; ;