(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide formate
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].[CH3:24][C:25]1[N:29]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([N:36]3[CH2:39][CH2:38][CH:37]3[C:40]([O-:42])=[O:41])[CH2:32][CH2:31]2)[S:27][N:26]=1.[Li+]>>[CH:40]([OH:42])=[O:41].[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]([CH:37]2[CH2:38][CH2:39][N:36]2[CH:33]2[CH2:32][CH2:31][N:30]([C:28]3[S:27][N:26]=[C:25]([CH3:24])[N:29]=3)[CH2:35][CH2:34]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
Product 1
Procedure
The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carboxylate 20D carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide formate 1:1 epimers as a white solid (73%). MS ISP (m/e): 618.3 (100) [(M+H)]]+.
Sources & evidence
- ORD record
- ord-b0a1b3c8b41342d8ada71bd3d281a05e
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802665B2
Reaction notes
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