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

HRID 2403216Notes

Reaction equation

HRID 2403216 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][NH:15][C@H:14]([C:17]([NH:19][C:20]2([C:23]#[N:24])[CH2:22][CH2:21]2)=[O:18])[CH2:13]1)(=[O:11])=[O:10].Cl.[CH3:26][C:27]1([CH3:39])[CH2:32][CH2:31][CH2:30][N:29]([C:33]2([C:36](O)=[O:37])[CH2:35][CH2:34]2)[CH2:28]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][N:15]([C:36]([C:33]2([N:29]3[CH2:30][CH2:31][CH2:32][C:27]([CH3:39])([CH3:26])[CH2:28]3)[CH2:35][CH2:34]2)=[O:37])[C@H:14]([C:17]([NH:19][C:20]2([C:23]#[N:24])[CH2:22][CH2:21]2)=[O:18])[CH2:13]1)(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 59543706(2S,4R)-4-(2-chloro-4-fluorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideHCID 866927981-(3,3-Dimethylpiperidin-1-yl)cyclopropanecarboxylic acid hydrochloride

Product 1

HCID 71711418(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(3,3-dimethylpiperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamideYield 15%

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7A with 1-(3,3-dimethylpiperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16M carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(3,3-dimethylpiperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide as a light yellow solid (15%). MS ISP (m/e): 533.3 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-a13fd4ccfdc74d4f99fbef148ccbd4a2
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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