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

HRID 887774Notes

Reaction equation

HRID 887774 reaction equation
[C:1]([CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[CH:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[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]=[CH:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 59145875ethyl 9-(cyanomethyl)-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 59145841ethyl 9-(2-aminoethyl)-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

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

Procedure

Ethyl 9-(cyanomethyl)-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (150 mg, 0.557 mmol) and Raney cobalt (1.5 g) were suspended in 2M ammonia/ethanol solution (28 mL), and the mixture 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 (150 mg, yield 99%).

Workup

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

Sources & evidence

ORD record
ord-3fcc9bd701a241f68e407bc3c5a64a06
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

Loading…