1H-Pyrrolo[2,3-b]pyridine-5-methanamine

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* = 470.9General 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.(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]+ = 483.30Boc-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%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%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

Molecular Weight:147.18
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:147.079647300
Monoisotopic Mass:147.079647300
Topological Polar Surface Area:54.7
Heavy Atom Count:11
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes