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

HRID 2403211Notes

Reaction equation

HRID 2403211 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C@H:11]2[CH2:15][NH:14][C@H:13]([C:16]([NH:18][C:19]3([C:22]#[N:23])[CH2:21][CH2:20]3)=[O:17])[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.[N:25]1([C:31]2([C:34](O)=[O:35])[CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C@H:11]2[CH2:15][N:14]([C:34]([C:31]3([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:32][CH2:33]3)=[O:35])[C@H:13]([C:16]([NH:18][C:19]3([C:22]#[N:23])[CH2:21][CH2:20]3)=[O:17])[CH2:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 86692782(2S,4R)-4-(3-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideHCID 866927871-(Piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride

Product 1

HCID 71711359(2S,4R)-4-(3-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamideYield 39%

Procedure

The reaction of (2S,4R)-4-(3-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7F with 1-(piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16A carried out according to the general procedure L yielded (2S,4R)-4-(3-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide as a white solid (39%). MS ISP (m/e): 505.2/507.3 (100/34) [(M+H)]+.

Sources & evidence

ORD record
ord-93f39c4ad0134af5b10cb064225f81d6
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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