(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → HCID 71711296, compound

HRID 2403207Notes

Reaction equation

HRID 2403207 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][N:29]([C:32]2([C:35](O)=[O:36])[CH2:34][CH2:33]2)[CH2:28][CH2:27]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:29]3[CH2:30][CH2:31][CH:26]([CH3:25])[CH2:27][CH2:28]3)[CH2:33][CH2:34]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 86692794HCID 86692794, compound

Product 1

HCID 71711296HCID 71711296, compoundYield 39%

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H with 1-(4-methylpiperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16I carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(4-methylpiperidin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide as an off-white solid (39%). MS ISP (m/e): 519.2 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-eb24c77d0a9b4ed7a3ec35194bf6e99e
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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