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[ CAS No. 17288-32-3 ] {[proInfo.proName]}

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Chemical Structure| 17288-32-3
Chemical Structure| 17288-32-3
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Product Details of [ 17288-32-3 ]

CAS No. :17288-32-3 MDL No. :MFCD11053752
Formula : C10H10N2O2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :NOWHXIDXMNNYBL-UHFFFAOYSA-N
M.W : 190.20 Pubchem ID :11579250
Synonyms :

Calculated chemistry of [ 17288-32-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.18
TPSA : 54.98 ?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) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 1.62
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 0.8
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.32
Solubility : 0.916 mg/ml ; 0.00481 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.78 mg/ml ; 0.0041 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0768 mg/ml ; 0.000404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 17288-32-3 ]

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 [ 17288-32-3 ]

* 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 [ 17288-32-3 ]

[ 17288-32-3 ] Synthesis Path-Downstream   1~12

  • 2
  • 2-[(E)-2-Chloro-pyridin-3-ylimino]-propionic acid ethyl ester [ No CAS ]
  • [ 17288-32-3 ]
  • 3
  • [ 17288-32-3 ]
  • [ 889658-85-9 ]
YieldReaction ConditionsOperation in experiment
61% With N-Bromosuccinimide; In dichloromethane; at 0 - 20℃; for 16h; N-Bromosuccinimide (15.4 g, 86.5 mmcl) was added to a 0 °C solution of ethyl 1 H-pyrrolo[3,2-b]pyridine-2-carboxylate (15.0 g, 78.9 mmol) in dichloromethane (150 mL), and the reaction mixture was stirred at room temperature for 16 hours. Afteraddition of dichloromethane (150 mL) and water (200 mL), the aqueous layer was extracted with dichloromethane (3 x 150 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (5 x 50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0percent to 50percent ethyl acetate in petroleum ether) afforded the product as a yellowsolid. Yield: 13 g, 48 mmol, 61percent. NMR (400 MHz, CDCI3) oe 9.94 (br s, 1 H), 8.65 (dd, J=4.5, 1.1 Hz, 1H), 7.78 (dd, J=8.4, 1.0 Hz, 1H), 7.31 (dd, J=8.4, 4.5 Hz, 1H), 4.49 (q, J=7.1 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H).
With pyridine; pyridinium hydrobromide perbromide; at 50℃; for 0.25h; Ethyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate 0.9 g of pyridinium tribromide in 5 ml of pyridine is added slowly, at 0° C. under argon, to a solution of 0.5 g of <strong>[17288-32-3]ethyl 1H-pyrrolo[3,2-b]pyridine-2-carboxylate</strong> in 12 ml of pyridine. The solution is then heated at 50° C. for 15 min and then poured onto 100 ml of ice-cold water. The solid formed is filtered off, washed with water, and filter-dried. After drying under vacuum, 0.56 g of ethyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate are obtained, the characteristics of which are as follows: MS (ES+) spectrum: m/z=270 [MH]+ Melting point=180° C. (Koefler bench). IR spectrum (KBr): 2983; 2841; 2681; 1711; 1513; 1374; 1346; 1261 1209; 1012; 767 and 651 cm-1
  • 4
  • [ 617-35-6 ]
  • [ 17288-32-3 ]
  • 5
  • [ 6298-19-7 ]
  • [ 17288-32-3 ]
  • 6
  • [ 677302-64-6 ]
  • [ 17288-32-3 ]
YieldReaction ConditionsOperation in experiment
86% With iron; acetic acid; In ethanol; for 2h;Heating / reflux; INTERMEDIATE 14 Ethyl pyrrolo[3,2-b]pyridine-2-carboxylate A mixture of Intermediate 13 (6.30 g, 26.5 mmol) and iron powder (325 mesh, 13.3 g, [238.] 2 mmol) in [ETOH] (100 [ML)] and [ACOH] (100 [ML)] was heated at reflux for 2 [H.)] Volatiles were removed in vacuo and toluene used to azeotrope excess [ACOH] (3 x 100 ml). The brown residue was suspended in EtOAc and passed through a plug of silica gel, eluting the desired product with EtOAc. Concentration of the eluent in vacuo gave the title compound as an off-white solid (4.32 g, 86percent). [8H] (d3-MeOD) [8.] [33-8.] 30 [(1H,] m), 7.84-7. 80 [(1H,] m), 7.22 [(1H,] dd, [J4.] 6,8. 4 Hz), 7.14 (1H, d, [J0.] 9 Hz), 4.33 (2H, q, J7.1 Hz), 1.33 (3H, t, J7.1 Hz). LCMS Method C [(: EST] RT 1.22 minutes, 191 [(M+H).]
  • 7
  • [ 17288-32-3 ]
  • [ 17288-35-6 ]
YieldReaction ConditionsOperation in experiment
82% 3-Amino-2-chloro-pyridine 4f (150 mg, 1.17 mmol), ethyl pyruvate 8 (0.25 ml, 2.00 mmol), pyridinium p-toluenesulfonate, (73 mg, 0.29 mmol) and tetraethoxy-silane (0.26 ml, 1.18 mmol) were suspended in 0.4 ml pyridine and stirred for 24 h at 20 °C. Afterwards Pd[P(C6H6)3]4 (70 mg, 0.06 mmol) and N,N-dicyclohexylmethylamine (0.35 ml, 2.06 mmol) were added and the reaction mixture was heated in a microwave oven to 160 °C for 20 min. The reaction mixture is diluted with 100 ml dichloromethan and extracted two times with 50 ml of a half saturated aqueous sodium hydrogencarbonat solution. The organic layer was dried with sodium sulfate, the solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P3, yielding 190 mg (1.00 mmol) of 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester. The ester was dissolved in 17 ml ethanol and 5 ml water. To this solution lithium hydroxide (120 mg, 5.00 mmol) was added. After 16 h the pH value of the reaction mixture was adjusted to pH 4 and the solvent is evaporated in vacuum. The crude product was purified using an acid ion exchanger (Strata-X-C, Phenomenex), yielding of 155 mg (82percent) of the title compound. Purity by method A1: >95percent; MS (ESI) m/z 163 (M + H)+; 1H NMR (DMSO) delta (ppm) 13.34 (br, 1H), 8.77 (d, J = 5.3 Hz, 1H), 8.53 (d, J = 8.3 Hz, 1H), 7.73 (dd, J = 5.4 Hz, J = 8.3 Hz, 1H), 7.33 (br, 1H); 13C NMR (500 MHz, DMSO) delta (ppm) 161.4 (s), 138.0 (s), 136.1 (s), 135.8 (s), 132.7 (s), 128.6 (s), 119.6 (s), 101.2 (s).
With sodium hydroxide; water; for 3h;Heating / reflux; A suspension of 1H PYRROLO [3,2-b] pyridine-2-carboxylic acid ethyl ester (Preparation 31,0. 34g, 1. 77MMOL) in aqueous sodium hydroxide solution (2M, lOmL) was heated under reflux for 3h and the resulting solution was allowed to cool to rt. The pH was adjusted to 4 by addition of glacial acetic acid. Excess acetic acid was removed in vacuo and the resulting suspension cooled to 0°C and then left standing at rt for 16h. The resulting beige precipitate was collected by filtration and dried to give the title compound as a beige solid. 8H (d6 DMSO): 7.12 (1H, s), 7.23 (1H, dd), 7.79 (1H, d), 8.42 (1H, dd).
  • 8
  • [ 17288-30-1 ]
  • [ 17288-32-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In ethanol; under 1034.32 - 1551.49 Torr; for 12h; To a suspension of 3- (3-nitropyridin-2-yl)-2-oxopropionic acid ethyl ester (Preparation 30, 1. 00G, 4. 20mmol) in ethanol (30mL, absolute) was added palladium (10percent on activated carbon, 447mg, 0. 42MMOL) and the reaction mixture placed under an atmosphere of hydrogen at a pressure of 20-30psi for 12h with vigorous stirring. The reaction mixture was filtered through celite, washing with ethyl acetate and the filtrate concentrated in vacuo to ca. 20mL. Water (150ML) was added and the mixture cooled to between 0°C and 5°C. The precipitate that formed was collected by filtration and dried to give the title compound as a beige SOLID. 8H (CDCl3): 1.44 (3H, t), 4.45 (2H, q), 7.25 (1H, dd), 7.39 (1H, s), 7.75 (1H, dd), 8.57 (1H, dd), 8.98 (1H, s).
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 1500.15 Torr; for 3h; Ethyl 1H-pyrrolo[3,2-b]pyridine-2-carboxylate 18.4 g of ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate and 5.5 g of 10percent palladium-on-charcoal are added to 500 ml of ethanol, and the reaction mixture is hydrogenated under 2 bar for 3 hours at 20° C. The reaction mixture is then filtered over a thin layer of silica gel and the filtrate is concentrated under reduced pressure, to give 14.1 g of ethyl 1H-pyrrolo[3,2-b]-pyridine-2-carboxylate, the characteristics of which are as follows: MS (ES+) spectrum: m/z=191 [MH]+ Melting point=176-178° C. (Koefler bench). 1H NMR spectrum (400 MHz, DMSO-d6, delta in ppm): 1.36 (t, J=7.0 Hz, 3H); 4.37 (q, J=7.0 Hz, 2H); 7.20 (broad s, 1H); 7.27 (dd, J=4.5 and 8.5 Hz, 1H); 7.84 (broad d, J=8.5 Hz, 1H); 8.45 (dd, J=1.5 and 4.5 Hz, 1H); 12.15 (broad m, 1H).
  • 9
  • [ 74-89-5 ]
  • [ 17288-32-3 ]
  • [ 853685-36-6 ]
YieldReaction ConditionsOperation in experiment
In water; at 20℃; for 16h; 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid methylamide, 6a-2 Stir 4-azaindole ester 4a-1 (R=Et, R4=H) neat in methylamine (40 wt percent solution in H2O) at rt for 16 h monitoring by tlc (10percent MeOH/CH2Cl2). When complete, dilute the reaction excess H2O, collect the precipitate by filtration and dry to provide 6a-2 (R2=NHCH3, R4=H) as an ivory colored solid (see General Synthetic procedure VI). MS Obs 176.07 (M+1).
  • 10
  • [ 17288-32-3 ]
  • [ 853685-35-5 ]
YieldReaction ConditionsOperation in experiment
~ 100% With ammonia; In water; at 20℃;Product distribution / selectivity; Suspend ester 4a-1 in concentrated NH4OH and stir at rt for several days monitoring by tlc (10percent MeOH/CH2Cl2). When complete, concentrate the reaction to minimum volume, dilute with excess H2O, collect the precipitate by filtration and dry to give amide 6a-1 (R2NH2, R4H) in about quantitative yield.
> 90% With ammonia; lithium chloride; In methanol; at 20℃; for 120h;Product distribution / selectivity; Stir ethyl 4-aza-2-indole carboxylate 4a (4.67 mmol) in 7N NH3/MeOH (20 mL) and add LICl (1.0 equiv, 4.67 mmol). Stir the reaction at rt for 5 days monitoring by tlc (10percent MeOH/CH2Cl2) during which time a precipitate forms. Concentrate the mixture to minimum volume, dilute with H2O and collect the solid by filtration. Wash the filter cake with H2O and dry under vacuum at 60° C. to afford primary amide 6a (>90percent).
44 - ~ 100% With ammonia; In methanol; at 20 - 55℃; under 517.162 - 1810.07 Torr;Product distribution / selectivity; 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid amide, 6a-1 (Scheme 1, step e) Add a solution of 7 N NH3 in MeOH (1.5 L, 10.5 mol, 20 equiv.) to a 3-L pressure reactor at rt and then add azaindole ester 4a-1 (100 g, 0.53 mol) as a solid. Slowly heat the slurry to 50° C. to afford a clear solution. One observes the initial pressure of 35 psi to drop to 16 psi over 4 h. Maintain the reaction at 50° C. for 49 h. One observes a final pressure of 10 psi. Monitor the progress of the reaction by HPLC (Agilent series 1100 using the following conditions: Waters Symmetry C8 (5mu) column (3.9*150 mm), flow rate at 1.0 mL/min, gradient elution conditions: time (minutes), water:acetonitrile-methanol ratio (acetonitrile-methanol used as a 1:1 solution) 0 min., 70:30; 10 min., 20:80; 15 min., 70:30; 20 min., 70:30; lambda1=210 nm, lambda2=220 nm, flow rate 1.0 mL/min, RT: ethyl ester 4a-1=5.6 min, methyl ester 5a-1=4.2 min, amide 6a-1=2.2 min). One observes the corresponding methyl ester 5a-1 being formed in the reaction and 5a-1 serves also as an intermediate in the reaction. Cool the reaction to 4° C. and isolate the resulting precipitate by vacuum filtration. Wash the filter cake with methyl tert-butyl ether (2*100 mL) and dry (40° C./0.1 in Hg) for 20 h to give 6a-1 as a gray solid (78.6 g, 93percent). 1H NMR (DMSO-d6) delta 7.17 (dd, 1H, J=4.5, 8.4 Hz), 7.53, 8.11 (2s, 2H, NH2), 7.76 (d, 1H, J=8.1 Hz), 8.37 (d, 1H, J=1.5 Hz), 11.72 (s, 1H, NH).
24% With ammonia; In ethanol; at 90℃; for 12h;Inert atmosphere; To a stirred solution of ethyl lH-pyrrolo[3,2-￡]pyridine-2-carboxylate 1 (300 mg, 1.58 mmol) in EtOH (6 mL) in a steel bomb at RT under an inert atmosphere, was added NH3 solution (18 mL). The reaction mixture was sealed and heated at 90 °C for 12 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was diluted with water (20 mL) and extracted with EtOAC (2 x 30 mL). The combined organic extracts were washed with brine (15 mL), dried (Na2S04), filtered, and concentrated under reduced pressure to afford compound 2 (60 mg, 24percent) as an off-white solid. 1H MR (500 MHz, OMSO-d6): delta 11.77 (br s, 1H), 8.38 (br d, J= 3.3 Hz, 1H), 8.11 (br s, 1H), 7.76 (br d, J= 8.3 Hz, 1H), 7.54 (br s, 1H), 7.25 (s, 1H), 7.18 (dd, J= 8.3, 4.4 Hz, 1H); LCMS Mass: 162.1 (M++l).

  • 11
  • [ 67-56-1 ]
  • [ 17288-32-3 ]
  • [ 394223-19-9 ]
YieldReaction ConditionsOperation in experiment
90 - 100% With potassium carbonate; at 55℃; for 1h; Add to ethyl 4-azaindole-2-carboxylate 4a (42.3 mmol) in MeOH (50 mL), K2CO3 (1.20 equiv, 50.7 mmol) and stir the suspension with heating to 55° C. for 1 h. Monitor the reaction by tlc (Et2O/hept). When complete, concentrate the reaction in vacuo, dilute with H2O and stir for 15 min. Collect the solid by filtration and dry in a vacuum oven at 65° C. for 3 h to afford about 90percent to about 100percent of the desired methyl 4-azaindole-2-carboxylate 5a.
  • 12
  • [ 23596-34-1 ]
  • [ 17288-32-3 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogen;palladium 10% on activated carbon; In ethanol; at 35 - 57℃; under 2327.23 Torr; for 4h;Parr reactor;Product distribution / selectivity; 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester, 4a-1 (Scheme 1, step c) Add to a 2 L thick-walled Parr reactor compound 3a-1 (56.8 g, 0.24 mol), ethanol (200 proof, 850 mL, 15 parts) and 10percent Pd/C (5.7 g, 10percent by wt.). Connect the reaction vessel to a Parr hydrogenator, flush with hydrogen and pressurize the orange slurry to 45 psi. Shake at rt for 1 h during which time the temperature rises to 57° C. When the temperature of the reaction mixture stabilizes at 35° C., slowly heat the reaction to 40° C. for 3 h. When the reaction is complete as determined by-TLC (silica gel, 1percent MeOH in CH2Cl2), cool the reaction mixture to rt, filter the slurry through Celite.(R)., and wash the filter cake with EtOH (4*200 mL). Concentrate the yellow filtrate to afford a solid (41.6 g), add ethyl acetate (302 mL) and heat on a steam bath. Cool the mixture to rt and add heptane (600 mL) to precipitate the product. Stir the mixture in an ice bath for 1 h, filter and wash the filter cake with heptane (100 mL). Dry the filter cake (50° C./0.1 in Hg) for 24 h to give 4a-1 as a light gray solid (36.6 g, 81percent yield). 1H NMR (DMSO-d6) 1.36 (t, 3H, J=7.0 Hz), 4.36 (q, 2H, J=7.0 Hz), 7.19 (s, 1H), 7.25 (dd, 1H, J=4.5, 8.1 Hz), 7.82 (d, 1H, J=8.1 Hz), 8.44 (d, 1H, J=4.5 Hz), delta 12.11 (s, 1H).
81% With titanium tetrachloride; tin(ll) chloride; In ethanol; for 4h;Heating / reflux;Product distribution / selectivity; Hydrogenate 3a-1 (20 g) over 10percent palladium on carbon (5.5 g) in EtOH (350 mL) at rt for 3 hours under 1200 psi. Filter the reaction mixture through Celite.(R). and concentrate the filtrate to give ester 4a-1 (R4H) in 39percent yield. Alternatively, reduce 3a-1 with SnCl2 (5.0 equiv), TiCl4 (2.5 equiv) in EtOH at reflux for 4 h, cool to ambient temperature, concentrate and purify by silica gel chromatography to provide ester 4a-1 (R4H) in 81percent yield. 1H NMR (DMSO-d6) delta 13.48 (bs, 1H), 8.80 (dd, 1H, J=0.7, 5.4 Hz), 8.56 (dd, 1H, J=0.7, 8.4 Hz), 7.80 (dd, 1H, J=5.5, 8.4 Hz), 7.37 (s, 1H), 4.40 (q, 2H, J=7.0 Hz), 1.38 (t, 3H, J=7.0 Hz).
39% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 62059.4 Torr; for 3h;Product distribution / selectivity; Hydrogenate 3a-1 (20 g) over 10percent palladium on carbon (5.5 g) in EtOH (350 mL) at rt for 3 hours under 1200 psi. Filter the reaction mixture through Celite.(R). and concentrate the filtrate to give ester 4a-1 (R4H) in 39percent yield. Alternatively, reduce 3a-1 with SnCl2 (5.0 equiv), TiCl4 (2.5 equiv) in EtOH at reflux for 4 h, cool to ambient temperature, concentrate and purify by silica gel chromatography to provide ester 4a-1 (R4H) in 81percent yield. 1H NMR (DMSO-d6) delta 13.48 (bs, 1H), 8.80 (dd, 1H, J=0.7, 5.4 Hz), 8.56 (dd, 1H, J=0.7, 8.4 Hz), 7.80 (dd, 1H, J=5.5, 8.4 Hz), 7.37 (s, 1H), 4.40 (q, 2H, J=7.0 Hz), 1.38 (t, 3H, J=7.0 Hz).
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