(2S,4R)-N-(1-cyanocyclopropyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide → (2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide

HRID 2403214Notes

Reaction equation

HRID 2403214 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].Cl.[N:28]1([C:34]2([C:37](O)=[O:38])[CH2:36][CH2:35]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)(=[O:16])=[O:15])[CH2:11][N:10]2[C:37]([C:34]2([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:35][CH2:36]2)=[O:38])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 86692786(2S,4R)-N-(1-cyanocyclopropyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamideHCID 866927871-(Piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride

Product 1

HCID 71711362(2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamideYield 56%

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide 7E with 1-(piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16A carried out according to the general procedure L yielded (2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide as a light yellow solid (56%). MS ISP (m/e): 539.3 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-21e390bc8bd842ad93a6bceb7abe845c
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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