Sodium hydride → 4-{5-[(3-Difluoromethoxy-benzenesulfonyl)-(3-fluoropropyl)amino]-2-methoxy-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 1710617Notes

Reaction equation

HRID 1710617 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH:31]([F:33])[F:32])[CH:25]=3)(=[O:23])=[O:22])[CH:17]=[CH:16][C:15]=2[O:34][CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:38][CH2:39][CH2:40][CH2:41]Br>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([N:20]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH:31]([F:32])[F:33])[CH:25]=3)(=[O:23])=[O:22])[CH2:41][CH2:40][CH2:39][F:38])[CH:17]=[CH:16][C:15]=2[O:34][CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 67699Propane, 1-bromo-3-fluoro-HCID 576995064-[5-(3-Difluoromethoxy-benzenesulfonylamino)-2-methoxy-phenyl]-piperazine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 670950644-{5-[(3-Difluoromethoxy-benzenesulfonyl)-(3-fluoropropyl)amino]-2-methoxy-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Procedure

The compound was prepared by analogy to the methods described for Preparation Example 2 and Example 1 from 4-{5-[(3-difluoromethoxybenzenesulfonyl)-amino]-2-methoxy-phenyl}-piperazine-1-carboxylic acid tert-butyl ester, which was reacted with sodium hydride and 3-fluoro-1-bromopropane to yield 4-{5-[(3-difluoromethoxy-benzenesulfonyl)-(3-fluoropropyl)amino]-2-methoxy-phenyl}-piperazine-1-carboxylic acid tert-butyl ester, which was deprotected to yield the title compound.

Workup

  1. customThe compound was prepared by analogy to the methods

Sources & evidence

ORD record
ord-a885cf78ac234106bae813193dd4c1b5
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

Loading…