Boron tribromide → 3-(4-((5-(2-(4-chloro-3-hydroxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)-N,N,N-trimethylpropan-1-aminium 2,2,2-trifluoroacetate

HRID 83836Notes

Reaction equation

HRID 83836 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:21]([S:30][CH2:31][C:32]3[C:37]([F:38])=[CH:36][C:35]([S:39]([NH:42][CH2:43][CH2:44][CH2:45][N+:46]([CH3:49])([CH3:48])[CH3:47])(=[O:41])=[O:40])=[CH:34][C:33]=3[F:50])=[N:20][CH:19]=2)([CH3:17])[CH3:16])=[CH:11][C:10]=1[O:51]C.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:21]([S:30][CH2:31][C:32]3[C:33]([F:50])=[CH:34][C:35]([S:39]([NH:42][CH2:43][CH2:44][CH2:45][N+:46]([CH3:47])([CH3:48])[CH3:49])(=[O:41])=[O:40])=[CH:36][C:37]=3[F:38])=[N:20][CH:19]=2)([CH3:16])[CH3:17])=[CH:11][C:10]=1[OH:51]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 867022303-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)-N,N,N-trimethylpropan-1-aminium 2,2,2-trifluoroacetate

Product 1

HCID 867022283-(4-((5-(2-(4-chloro-3-hydroxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)-N,N,N-trimethylpropan-1-aminium 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by treating 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonamido)-N,N,N-trimethylpropan-1-aminium 2,2,2-trifluoroacetate with boron tribromide in DCM, followed by standard workup and then purified by preparative HPLC. MS (EI) m/z 667.4 (M+).

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-367cd2da4f7741ae8857b4f9f0aef196
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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