(2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylsulfonyl)pyrrolidine-2-carboxamide → (2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-(2-(trifluoromethoxy)phenylsulfonyl)pyrrolidine-2-carboxamide

HRID 2403213Notes

Reaction equation

HRID 2403213 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].Cl.[N:29]1([C:35]2([C:38](O)=[O:39])[CH2:37][CH2:36]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][C:24]([F:27])([F:25])[F:26])(=[O:16])=[O:15])[CH2:11][N:10]2[C:38]([C:35]2([N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:36][CH2:37]2)=[O:39])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 59543578(2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylsulfonyl)pyrrolidine-2-carboxamideHCID 866927871-(Piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride

Product 1

HCID 71711361(2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-(2-(trifluoromethoxy)phenylsulfonyl)pyrrolidine-2-carboxamideYield 61%

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylsulfonyl)pyrrolidine-2-carboxamide 7D with 1-(piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride 16A carried out according to the general procedure L yielded (2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-(2-(trifluoromethoxy)phenylsulfonyl)pyrrolidine-2-carboxamide as a light yellow solid (61%). MS ISP (m/e): 555.3 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-a8d23b7b84e847d096841fa4bc8c3a74
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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