tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate → 3-[2-(1-t-Butoxycarbonylpyrrolidin-3-ylmethoxy)-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

HRID 1434852Notes

Reaction equation

HRID 1434852 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([C:25]2[C:30]([NH:31][C:32](=[S:41])[C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:34]=3O)=[CH:29][CH:28]=[CH:27][N:26]=2)=[O:24])=[N:20][CH:21]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:34]2[CH:35]=[C:36]([CH3:39])[CH:37]=[CH:38][C:33]=2[C:32]([NH:31][C:30]2[C:25]([C:23]([NH:22][C:19]3[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][N:20]=3)=[O:24])=[N:26][CH:27]=[CH:28][CH:29]=2)=[S:41])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 136348818N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide

Product 1

HCID 866200073-[2-(1-t-Butoxycarbonylpyrrolidin-3-ylmethoxy)-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

Procedure

Using a procedure analogous to Example 38-D, 1-t-butoxycarbonylpyrrolidin-3-ylmethanol (Isomer II), from the prior example, and N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide gave the title compound as a white solid (1.0 g).

Sources & evidence

ORD record
ord-6df0445ef8964dd38a3a3fc88063e9d4
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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