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

HRID 887776Notes

Reaction equation

HRID 887776 reaction equation
[C:1]([CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([CH3:21])[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.CO.[Co]>[NH2:2][CH2:1][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([CH3:21])[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 59145857ethyl 9-(cyanomethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 59145868ethyl 9-(2-aminoethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 21705897Ammonia methanolSolvent

Procedure

Ethyl 9-(cyanomethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (145 mg, 0.512 mmol) and Raney cobalt (1.5 g) were suspended in 2M ammonia/methanol solution (50 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 14 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (145 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-2a5b1e5baa0f4c81b6ac02c019e3fca5
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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