methyl 9-(cyanomethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate → methyl 9-(2-aminoethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 887797Notes

Reaction equation

HRID 887797 reaction equation
[C:1]([CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:15]=3[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1)#[N:2]>N.C(O)C.[Co]>[NH2:2][CH2:1][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:15]=3[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 59145843methyl 9-(cyanomethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 59145919methyl 9-(2-aminoethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 97.2%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

Methyl 9-(cyanomethyl)-2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (300 mg, 0.905 mmol) and Raney cobalt (3 g) were suspended in 2M ammonia/ethanol solution (15 mL), and the suspension was stirred under a hydrogen atmosphere at room temperature for 12 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (295 mg, yield 97%).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ffbfc21b01d14c45892721ae76958a56
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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