(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → HCID 71711295, compound

HRID 2403206Notes

Reaction equation

HRID 2403206 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.[C:25]1([CH:31]2[CH2:36][CH2:35][N:34]([C:37]3([C:40](O)=[O:41])[CH2:39][CH2:38]3)[CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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:40]([C:37]2([N:34]3[CH2:33][CH2:32][CH:31]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:36][CH2:35]3)[CH2:39][CH2:38]2)=[O:41])[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 86692793HCID 86692793, compound

Product 1

HCID 71711295HCID 71711295, compoundYield 52%

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H with 1-(4-phenylpiperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16H carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(4-phenylpiperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide as an off-white solid (52%). MS ISP (m/e): 581.2 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-4303cb9a0e524b16b5d18a538d39f2a8
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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