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

HRID 2403212Notes

Reaction equation

HRID 2403212 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:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].Cl.[N:25]1([C:31]2([C:34](O)=[O:35])[CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]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:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=3)(=[O:16])=[O:15])[CH2:11][N:10]2[C:34]([C:31]2([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:32][CH2:33]2)=[O:35])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

3

Reactant 2

HCID 86692783(2S,4R)-N-(1-cyanocyclopropyl)-4-tosylpyrrolidine-2-carboxamideHCID 866927871-(Piperidin-1-yl)cyclopropanecarboxylic acid hydrochloride

Product 1

HCID 71711360(2S,4R)-N-(1-cyanocyclopropyl)-1-(1-(piperidin-1-yl)cyclopropanecarbonyl)-4-tosylpyrrolidine-2-carboxamideYield 40%

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-tosylpyrrolidine-2-carboxamide 7G 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-tosylpyrrolidine-2-carboxamide as a light yellow solid (40%). MS ISP (m/e): 485.4 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-5188a5bcf91148e9a3bce7ebe2c7ecaf
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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