3-(Difluoromethoxy)benzenesulfonyl chloride → HCID 67094709, compound

HRID 1710612Notes

Reaction equation

HRID 1710612 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[C:16]([F:23])[C:15]=2[O:24][CH3:25])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[F:26][CH:27]([F:39])[O:28][C:29]1[CH:30]=[C:31]([S:35]([Cl:38])(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>>[ClH:38].[F:39][CH:27]([F:26])[O:28][C:29]1[CH:30]=[C:31]([S:35]([NH:20][C:18]2[CH:19]=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:15]([O:24][CH3:25])=[C:16]([F:23])[CH:17]=2)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 27782263-(Difluoromethoxy)benzenesulfonyl chlorideHCID 67094969HCID 67094969, compound

Product 1

HCID 67094709HCID 67094709, compound

Procedure

The compound was prepared by analogy to Example 7, starting from commercially available 1-bromo-3-fluoro-2-methoxy-5-nitrobenzene, which was reacted with tert.butyloxycarbonyl-piperazine by analogy to preparation example 3.1 top yield 1-(N-boc-piperazin-4-yl)-3-fluoro-2-methoxy-5-nitrobenzene. Reduction of the nitro group to the corresponding aniline by analogy to preparation example 3.2, subsequent coupling with commercially available 3-difluoromethoxybenzenesulfonylchloride by analogy to preparation example 1.4, and final deprotection of the tert.-butoxycarbonyl group under acidic conditions by analogy to example 1 yielded the title compound.

Workup

  1. customto preparation example 1.4

Sources & evidence

ORD record
ord-903c7b67203f499e8fc5c361e71b3476
Source dataset
uspto-grants-2010_09
Patent number
US07790727B2

Reaction notes

Loading…