(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → HCID 71711299, compound

HRID 2403209Notes

Reaction equation

HRID 2403209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][NH:14][C@H:13]([C:16]([NH:18][C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[O:17])[CH2:12]1)(=[O:10])=[O:9].Cl.[CH3:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[C:32]1([C:35](O)=[O:36])[CH2:34][CH2:33]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:35]([C:32]2([N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]3[CH3:25])[CH2:34][CH2:33]2)=[O:36])[C@H:13]([C:16]([NH:18][C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[O:17])[CH2:12]1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 46946413(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideHCID 86692796HCID 86692796, compound

Product 1

HCID 71711299HCID 71711299, compoundYield 33%

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H with 1-(2-methylpiperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16L carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(2-methylpiperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide as a yellow solid (33%). MS ISP (m/e): 519.3 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-5718f945f29e49e5a9f0c033777adf77
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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