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CAS No. : | 267876-25-5 | MDL No. : | MFCD09475794 |
Formula : | C8H9N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QIPKJJHSPMUFFY-UHFFFAOYSA-N |
M.W : | 147.18 | Pubchem ID : | 12096224 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.77 |
TPSA : | 54.7 Ų |
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) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 1.11 |
Log Po/w (XLOGP3) : | 0.17 |
Log Po/w (WLOGP) : | 0.87 |
Log Po/w (MLOGP) : | 0.44 |
Log Po/w (SILICOS-IT) : | 1.63 |
Consensus Log Po/w : | 0.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.4 |
Solubility : | 5.87 mg/ml ; 0.0399 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.88 |
Solubility : | 19.6 mg/ml ; 0.133 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.94 |
Solubility : | 0.171 mg/ml ; 0.00116 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Boc-4-fluoro-Phe-OH (459mg, 1.62mmol) was dissolved in CH2C12 (30mls). To this solution was added HBTU (615mg, 1.62mmol) and triethylamine (490mg, 4.86mmol). After 15mins C-(lH-pyrrolo[2,3-b]pyridin-5-yl)-methylamine (250mg, 1.7mmol) was added. After 2 hrs at room temperature the reaction mixture was diluted with CHC13 (150mls), this solution was washed with sat. NaHC03 (lx50mls), water (lx50mls), brine (lx50mls), dried (Na2S04) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 10% MeOH, 90% CH2C12, fractions combined and evaporated in vacuo to give a white solid identified as the title compound.Yield = 275mg, 0.67mmol, 41%[M+H]+ = 413.21 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Boc-l-Nal-OH (643mg, 2.04mmol) was dissolved in CH2C12 (30mls). To this solution was added HBTU (773mg, 2.04mmol) and triethylamine (516mg, 5.10mmol). After 15mins C-(lH-pyrrolo[2,3-b]pyridin-5-yl)-methylamine (250mg, 1.7mmol) was added. After 2 hrs at room temperature the reaction mixture was diluted with CHC13 (150mls), this solution was washed with sat. NaHC03 (lx50mls), water (lx50mls), brine (lx50mls), dried (Na2S04) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 1% MeOH, 99% CHC13, fractions combined and evaporated in vacuo to give a white solid identified as the title compound.Yield = 520mg, 1.17mmol, 69%[M+H]+ = 445.20 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Boc-3,4-dichloro-Phe-OH (l .Og, 3.32mmol) was dissolved in CH2C12 (lOOmls) and DMF (5mls). To this solution was added HBTU (1.26g, 3.32mmol) and triethylamine (l .OOg, 9.95mmol). After 15mins C-(lH-Pyrrolo[2,3-b]pyridin-5-yl)-methylamine (512mg, 3.49mmol) was added. After 2 hrs at room temperature the reaction mixture was diluted with CHC13 (150mls), this solution was washed with sat. NaHC03 (lx50mls), water (lx50mls), brine (lx50mls), dried ( a2S04) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 10% MeOH, 90% CH2C12, fractions combined and evaporated in vacuo to give a white solid identified as the title compound.Yield = 1.24g, 2.88mmol, 87%[M+H]+ = 431.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Boc-3,4-difluoro-Phe-OH (l .Og, 3.32mmol) was dissolved in CH2Cl2(100mls) and DMF (5mls). To this solution was added HBTU (1.26g, 3.32mmol) and triethylamine(1.00g, 9.95mmol). After 15mins C-(lH-pyrrolo[2,3-b]pyridin-5-yl)-methylamine (512mg, 3.49mmol) was added. After 2 hrs at room temperature the reaction mixture was diluted with CHC13 (150mls), this solution was washed with sat. NaHC03 (lx50mls), water (lx50mls), brine (lx50mls), dried (Na2S04) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 10% MeOH, 90% CH2CI2, fractions combined and evaporated in vacuo to give a white solid identified as the title compound. Yield = 1.24g, 2.88mmol, 87% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20.0℃; for 3h; | (R)-2-tert-Butoxycarbonylamino-3,3-dicyclohexyl-propionic acid (721mg, 2.04mmol) was dissolved in CHaCb Omls). Triethylamine (516mg, 5.10mmol) and HBTU (773mg, 2.04mmol) was added followed by C-(lH-pyrrolo[2,3-b]pyridin-5-yl)-methylamine (250mg, L70mmol). After 3 hours at room temperature the reaction mixture was diluted with CHCI3 (50mls), this solution was washed with sat. NaHC03 (lx20mls), water (lx20mls), brine (lx20mls), dried (Na2S04) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 10% hexane, 90% CHCI3, fractions combined and evaporated in vacuo to give a colourless oil identified as the title compound.Yield = 817mg, 1.69mmol, 100%[M+H]+ = 483.30 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃; for 16h; | General procedure: To solutions of 2-(2,4-dichlorophenoxy)propanoic acid (100 mg,0.43 mmol) in DMF (2 mL) were added 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (HATU; 200 mg,0.53 mmol), the corresponding benzylamines (0.50 mmol), anddiisopropylethylamine (100 lL, 0.57 mmol). The resulting mixtureswere stirred at room temperature for 16 h, then poured intowater (20 mL). The aqueous mixtures were then stirred at roomtemperature until solids precipitate. The solids were filtered,rinsed with water, and dried to provide solids that were recrystallizedfrom CH2Cl2/hexane to provide the products 34a-y. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; for 18h; | l-(2-Pyrrolidin-1-yl-pyrimidin-5-ylmethyl)-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (1H- pyrrolo[2,3-b]pyridin-5-ylmethyl)-amide l-(2-Pyrrolidin-1-yl-pyrimidin-5-ylmethyi)-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (596 mg, 1.75 mmol) was dissolved in DCM (50 mL) and DMF (2.5 mL). This solution was cooled to 0 C. 5-Aminomethyl azaindole (308 mg, 2.10 mmol) was added followed by HOBt (260 mg, 1.92 mmol) and triethylamine (530 mg, 5.24 mmol). EDC (402 mg, 2.1 mmol) was added. After 18 hrs at 0 'C to rt reaction mixture was diluted with chloroform (200 mL), washed with NaHCOj (lx30mL), water (lx30mL), brine (lx30mL) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eiuent 6%MeOH, 94% CHCIs to give a white solid identified as l-(2-pyrrolidin-1-yl-pyrimidin-5-ylmethyl)-3-trifluoromethyl-1H- pyrazole-4-carboxylic acid (1H-pyrroio[2,3-b]pyridin-5-ylmethyi)-amide (620 mg, 75% yield). MH* = 470.9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20 - 23℃; | 49 EXAMPLE 49 PREPARATION OF N-((1H-PYRROLO[2,3-B]PYRIDIN-5-YL)METHYL)-2-(6-(1-METHYL-1H- PYRAZOL-4-YL)-2-OXO-3-(PHENETHYLAMINO)PYRAZIN-1(2H)-YL)ACETAMIDE (COMPOUND 131) To a solution of 2-(6-(1-methyl-1H-pyrazol-4-yl)-2-oxo-3-(phenethylamino)pyrazin-1(2H)-yl)acetic acid (25 mg, 0.07 mmol, prepared according to Example 41) and (1H-pyrrolo[2,3-b]pyridin-5-yl)methanamine (13 mg, 0.085 mmol) in DMF (0.23 mL) was added HATU (40 mg, 0.11 mmol) and DIEA (60 L, 0.35 mmol).The reaction was stirred at RT until completion, concentrated, and the residue was purified by chromatography (amine column: hepanes then 0-20% MeOH-CH2Cl2) to afford N-((1H-pyrrolo[2,3-b]pyridin-5-yl)methyl)-2-(6-(1-methyl-1H-pyrazol-4-yl)-2-oxo-3-(phenethylamino)pyrazin-1(2H)-yl)acetamide (15.9 mg, 47% yield). |
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