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[ CAS No. 145901-11-7 ] {[proInfo.proName]}

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Chemical Structure| 145901-11-7
Chemical Structure| 145901-11-7
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Quality Control of [ 145901-11-7 ]

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Product Details of [ 145901-11-7 ]

CAS No. :145901-11-7 MDL No. :MFCD08272224
Formula : C7H7N3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :OHPOAAFCWFZVPF-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :10419227
Synonyms :

Calculated chemistry of [ 145901-11-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.5
TPSA : 54.7 ?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) : -6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.02
Log Po/w (XLOGP3) : 0.96
Log Po/w (WLOGP) : 1.15
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.94
Solubility : 1.54 mg/ml ; 0.0116 mol/l
Class : Very soluble
Log S (Ali) : -1.7
Solubility : 2.68 mg/ml ; 0.0201 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.404 mg/ml ; 0.00303 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 145901-11-7 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338-P310 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 145901-11-7 ]

* 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 [ 145901-11-7 ]

[ 145901-11-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 143468-13-7 ]
  • [ 145901-11-7 ]
  • 2
  • [ 145901-11-7 ]
  • [ 99-63-8 ]
  • N,N'-bis(1H-pyrrolo<2,3-b>pyridin-6-yl)-1,3-benzenedicarboxamide [ No CAS ]
  • 3
  • [ 108-24-7 ]
  • [ 145901-11-7 ]
  • N-(1-acetyl-1H-pyrrolo[2,3-b]pyridin-6-yl)acetamide [ No CAS ]
  • 4
  • 6-azaindole-N-oxide m-chlorobenzoate [ No CAS ]
  • [ 145901-11-7 ]
YieldReaction ConditionsOperation in experiment
To a solution of O-methyl-nu-oxide salt intermediate in AcCN (10 ml) obtained as above from 1.37 g (4.71 mmol) N-oxide m-CBA salt and dimethylsulfate (0.49 ml, 1.05 eq.) was added a solution OfNH3 in dry MeOH (7M, Aldrich, 15 ml) under cooling in an icebath. The brown mixture was stirred in a sealed vial at 70 0C overnight. After evaporation of the solvent and aq. workup as above, the crude was purified by silica gel chromatography to give a light-brown, cryst. solid. HR-MS calculated for [MH]+: 134.07127, found: 134.07150.
  • 5
  • CH3O4S(1-)*C7H5ClO2*C8H9N2O(1+) [ No CAS ]
  • [ 145901-11-7 ]
  • 6
  • [ 271-63-6 ]
  • [ 145901-11-7 ]
YieldReaction ConditionsOperation in experiment
To a solution of commercially available 7-azaindole (5 g, 42.3 mmol) in diethyl ether (350 mL) was added m-chloro perbenzoic acid (11 g, 63.4 mmol) in portions at room temperature. The reaction mixture was stirred at room temperature for 5 h. The precipitated product was filtered off and washed with diethyl ether (50 mL). The solid was collected and dissolved in a mixture of water/acetone (50 mL/10 mL) with heating. The mixture was cooled to 5 C. and the crystallized product was filtered and air dried to afford the title compound (11.7 g, 96%).1H-NMR (400 MHz, CDCl3): delta=6.59 (d, 1H), 7.07 (dd, 1H), 7.46 (d, 1H), 7.66 (d, 1H), 8.14 (d, 1H), 12.4 (s, 1H).Step BTo a suspension of the title compound from Step A above (2 g, 6.92 mmol) in dry acetonitrile (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C. for 8 h. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C. under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was added to each tube. The sealed tubes were heated at 50-60 C. for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2CO3 solution, water, and brine. The organic phase was dried over Na2SO4. The solvent was evaporated and the crude product was purified by chromatography on silica using ethyl acetate to afford the title compound (0.5 g, 54%).1H-NMR (400 MHz, CDCl3): delta=4.33 (m, 2H), 6.35 (dd, 1H), 6.38 (d, 1H), 6.99 (dd, 1H), 7.71 (d, 1H).
  • 7
  • 1H-pyrrolo[2,3-b]pyridine 1-oxide meta-chlorobenzoic acid salt [ No CAS ]
  • [ 145901-11-7 ]
YieldReaction ConditionsOperation in experiment
54% To a suspension of the compound from Step A above (2 g, 6.92 mmol) in dry acetonitrile (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C. for 8 hours. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C. under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was introduced in each tube. The tubes were sealed. The sealed tubes were heated at 50 to 60 C. for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2CO3 solution, water, and brine. The organic phase was dried over Na2SO4. The solvent was evaporated and crude product was purified on silica gel (ethyl acetate) to give the title compound (0.5 g, 54%).1H-NMR (400 MHz, CDCl3): =7.71 (d, 1H), 6.99 (dd, 1H), 6.38 (d, J=8.4 Hz, 1H), 6.35 (dd, 1H), 4.33 (m, 2H).
54% Step B To a suspension of the compound from Step A above (2 g, 6.92 mmol) in dry acetonitrile (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C for 8 hours. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was introduced in each tube. The tubes were sealed. The sealed tubes were heated at 50 to 60 C for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2CO3 solution, water, and brine. The organic phase was dried over Na2SO4. The solvent was evaporated and crude product was purified on silica gel (ethyl acetate) to give the title compound (0.5 g, 54 %). 1H-NMR (400 MHz, CDCl3): delta = 7.71 (d, 9H), 6.99 (dd, 1H), 6.38 (d, J = 8.4Hz, 1H), 6.35 (dd, 1H), 4.33 (m, 2H)
54% Step B; To a suspension of the title compound from Step A above (2 g, 6.92 mmol) in dry acetonit ie (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C for 8 h. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was added to each tube. The sealed tubes were heated at 50-60 C for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2C03 solution, water, and brine. The organic phase was dried over Na2S04. The solvent was evaporated and the crude product was purified by chromatography on silica using ethyl acetate to afford the title compound (0.5 g, 54%).1H-NMR (400 MHz, CDCI3): delta = 4.33 (m, 2H), 6.35 (dd, 1 H), 6.38 (d, 1 H), 6.99 (dd, 1 H), 7.71 (d, 1 H).
48% With dimethyl sulfate; In acetonitrile;Reflux; The suspension of compound 3 (1.89g, 11.8 mmol) in dry CH3CN (15 ml) was added dimethylsulfate and heated the reaction mixture at 80 C for overnight. The reaction mixture was cooled to room temperature. Then, the reaction mixture was partitioned into 3 sealed tubes and cooled to ice bath temperature. The 7N NH3 solution in MeOH (5 ml) was introduced to each tube at 0 C temperature and sealed the tubes. The reaction mixture was heated at 70 C for 2d. The reaction mixture was concentrated under reduced pressure and the residue was crystallized from ethyl acetate and heptane mixture to give compound 5 (0.9 g, 48%). 1H-NMR (400 MHz, CDCl3): delta= 7.83 (s, 1H), 7.64 (d, J = 8.4Hz, 1H), 6.42 (d, J = 8.8Hz, 1H), 6.00 (s, 1H) 3.33 (bs, 2H).
44.6% Under nitrogen atmosphere in anhydrous acetonitrile 1H-pyrrolo[2,3-b]pyridine-N-oxide meta-chlorobenzoic acid (12.3 g, 42.5mmol) and dimethyl sulfate (4.5 ml, 46.3 mmol) the suspension was 55-60 C It was stirred for 14 hours in . The reaction mixture was transferred to a sealed tube was cooled to 0 ~ 4 was slowly added a solution of ammonia (7M, 100 ml) in methanol. The reaction mixture was stirred at 50 ~ 55 C for 24 hours. Distilled off and the solvent of the reaction and extracted with dichloromethane (100 ml) and 10% aqueous potassium carbonate solution (25 ml) to the remaining residue and the water layer was further extracted three times with dichloromethane (50ml). All the organic layer was removed with 10% carbonate kalryul solution and saturated brine, washed with water once and the solvent collecting behind a dry, filtered over anhydrous magnesium sulfate filtrate. The residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1: 2) to afford the title compound as a yellow crystalline solid (2.5g, 44.6% yield).
316 mg Step 4 1H-Pyrrolo[2,3-b]pyridin-6-ylamine 1H-Pyrrolo[2,3-b]pyridine 7-oxide, 3-chlorobenzoic acid complex (1.5 g, 5.16 mmol) was suspended in acetonitrile (10 mL). Dimethyl sulfate (0.54 mL, 5.68 mmol) was added and the reaction mixture was warmed to 60 C. After 16 h, the mixture was transferred to a thick-walled pressure tube and 7M ammonia in methanol solution (11 mL) was added. The tube was sealed and warmed to 55 C. After 16 h, the solvent was evaporated and the residue was taken up in dichloromethane and 10% sodium carbonate solution. The aqueous layer was extracted with dichloromethane, and then the combined organic layers were washed successively with saturated aqueous sodium bicarbonate solution, water and brine. The organic phase was dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by chromatography (silica, 10 to 80% ethyl acetate in hexanes) gave 1H-pyrrolo[2,3-b]pyridin-6-ylamine (316 mg, 46%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.73 (br. s., 1H) 7.70 (d, J=8.3 Hz, 1H) 6.99 (d, J=3.5 Hz, 1H) 6.38 (d, J=8.3 Hz, 1H) 6.36 (d, J=3.5 Hz, 1H) 3.82 (br. s., 2H).

  • 8
  • [ 1015609-27-4 ]
  • [ 145901-11-7 ]
  • [ 1342811-66-8 ]
YieldReaction ConditionsOperation in experiment
30% With sodium t-butanolate; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere; Preparative Example 60; Step AStep AAn oven-dried Schlenk flask was evacuated and back filled with argon gas. The procedure was repeated for 3-4 times. At room temperature dioxane (3 ml_) was added by a syringe and degassed by bubbling argon through the mixture. Then 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (XPhos, 0.054 g, 0.1 12 mmol) and palladium(ll) acetate (0.009 g, 0.037mmol) were added together. The mixture was heated at 110 C for 1 minute. The reaction mixture became a clear red color solution. Then the title compound from Preparative Example 3 (0.050 g, 0.375 mmol), commercially available 6-bromo-1-(triisopropylsilyl)-1 /-/-pyrrolo[3,2- ￡>]pyridine (0.132 g, 0.375 mmol) and sodium tert butoxide (0.12 g, 1.25 mmol) were added together under an argon atmosphere. The reaction mixture was heated at 110 C for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water, brine, and was dried over Na2S04. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate to afford the title compound (0.045 g, 30 %). H-NMR (400 MHz, CDCI3): delta = 1.13 (d, 18H), 1.61-1.68 (m, 3H), 6.35 (dd, 1H), 6.60 (d, 1H), 6.80 (d, 1H), 6.94 (dd, 1H), 7.10 (brs, 1H), 7.39 (d, 1H), 7.73 (d, 1H), 8.20 (s, 1H), 8.54 (s, 1H), 9.27 (s, 2H)
30% With sodium t-butanolate; XPhos;palladium diacetate; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere; An oven-dried Schlenk flask was evacuated and back filled with argon gas. The procedure was repeated for 3-4 times. At room temperature dioxane (3 mL) was added by a syringe and degassed by bubbling argon through the mixture. Then 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.054 g, 0.112 mmol) and palladium(II) acetate (0.009 g, 0.037 mmol) were added together. The mixture was heated at 110 C. for 1 minute. The reaction mixture became a clear red color solution. Then the title compound from Preparative Example 3 (0.050 g, 0.375 mmol), commercially available 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridine (0.132 g, 0.375 mmol) and sodium tert butoxide (0.12 g, 1.25 mmol) were added together under an argon atmosphere. The reaction mixture was heated at 110 C. for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water, brine, and was dried over Na2SO4. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate to afford the title compound (0.045 g, 30%).1H-NMR (400 MHz, CDCl3): delta=1.13 (d, 18H), 1.61-1.68 (m, 3H), 6.35 (dd, 1H), 6.60 (d, 1H), 6.80 (d, 1H), 6.94 (dd, 1H), 7.10 (brs, 1H), 7.39 (d, 1H), 7.73 (d, 1H), 8.20 (s, 1H), 8.54 (s, 1H), 9.27 (s, 2H)
30% With palladium diacetate; sodium t-butanolate; XPhos; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere; An oven-dried Schlenk flask was evacuated and back filled with argon gas. The procedure was repeated for 3-4 times. At room temperature dioxane (3 mL) was added by a syringe and degassed by bubbling argon through the mixture. Then 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (XPhos, 54 mg, 0.112 mmol) and palladium(II) acetate (9 mg, 0.037mmol) were added together. The mixture was heated at 110 oC for 1 minute. The reaction mixture became a clear red color solution. Then compound 5 (50 mg, 0.375 mmol), commercially available 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridine 31 (132 mg, 0.375 mmol) and sodium tert butoxide (120 mg, 1.25 mmol) were added together under an argon atmosphere. The reaction mixture was heated at 110 oC for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water, brine, and was dried over Na2SO4. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate to afford the compound 38a (45 mg, 30 %). 1H-NMR (400 MHz, CDCl3): delta = 9.27 (s, 2H), 8.54 (s, 1H), 8.20 (s, 1H), 7.73 (d, 1H), 7.39 (d, 1H), 7.10 (br-s, 1H), 6.94 (dd, 1H), 6.80 (d, 1H), 6.60 (d, 1H), 6.35 (dd, 1H), 1.68-1.61 (m, 3H), 1.13 (d, 18H).
  • 9
  • [ 1403888-69-6 ]
  • [ 145901-11-7 ]
  • [ 1403886-21-4 ]
  • 10
  • [ 1403888-69-6 ]
  • [ 145901-11-7 ]
  • C26H22N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example No. 130Preparation of (8-Methoxy-2H-pyrazolo [3, 4-c] quinolin-4 -yl) - (IH-pyrrolo [2 , 3 -b] pyridin-6-yl) -amineIH-pyrrolo [2 , 3 -b] pyridin-6-amine (0.4 mmol 2 eq.,) was dissolved in THF (dry, 3mL) in a microwave vial (2-5mL) LiHMDS 2M in THF (0.6 mmol 4eq.) was added. The mixture was stirred for 20 min at r.t. and then added to a solution of 4-chloro-8- methoxy-2- (4 -methoxybenzyl) -2H-pyrazolo [3 , 4-c] quinoline (0.16 mmol, leq.) in pyridine (2mL) . The reaction mixture was irradiated in a microwave reactor for 20 min at 200C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was concentrated and purified by semi -preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 330.1404 g/molHPLC-MS : analytical method Brt: 2.352 min - found mass: 331.1 (m/z+H)
  • 11
  • [ 145901-11-7 ]
  • [ 1446791-69-0 ]
  • 12
  • [ 145901-11-7 ]
  • [ 1446791-71-4 ]
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; ;