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

HRID 1710616Notes

Reaction equation

HRID 1710616 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+].[CH2:38](Br)[CH3:39]>>[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])[CH2:38][CH3:39])[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 6332Ethyl BromideHCID 24758Sodium hydrideHCID 576995064-[5-(3-Difluoromethoxy-benzenesulfonylamino)-2-methoxy-phenyl]-piperazine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 670949414-{5-[(3-Difluoromethoxy-benzenesulfonyl)-ethyl-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 Examples 1 and 5 from 4-{5-[(3-difluoromethoxybenzenesulfonyl)-amino]-2-methoxyphenyl}-piperazine-1-carboxylic acid tert-butyl ester, which was reacted with sodium hydride and ethylbromide to yield 4-{5-[(3-difluoromethoxy-benzenesulfonyl)-ethyl-amino]-2-methoxy-phenyl}-piperazine-1-carboxylic acid tert-butyl ester, which was deprotected and subsequently subjected to reductive amination with aqueous formaldehyde and sodium triacetoxyborohydride as described for example 5 to yield the title compound.

Workup

  1. customThe compound was prepared by analogy to the methods

Sources & evidence

ORD record
ord-e04055738cdf45cd81fafd4033cb287f
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

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