(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → HCID 71664742, compound

HRID 2403197Notes

Reaction equation

HRID 2403197 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].[Na+].[S:25]1[CH2:30][CH2:29][N:28]([C:31]2([C:34]([O-])=[O:35])[CH2:33][CH2:32]2)[CH2:27][CH2:26]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:34]([C:31]2([N:28]3[CH2:27][CH2:26][S:25][CH2:30][CH2:29]3)[CH2:33][CH2:32]2)=[O:35])[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 89755390HCID 89755390, compound

Product 1

HCID 71664742HCID 71664742, compoundYield 46%

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H with 1-thiomorpholinocyclopropanecarboxylic acid sodium salt 16C carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-thiomorpholinocyclopropanecarbonyl)pyrrolidine-2-carboxamide as a light brown solid (46%). MS ISP (m/e): 523.3 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-ac9fd6a942bf451896e1165917596fd5
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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