Trifluoroacetic acid → 5-Chloro-2-fluoro-4-{[(1S*,2S*)-2-(1H-imidazol-1-yl)cyclohexyl]oxy}-N-(1,3-thiazol-4-yl)benzenesulfonamide

HRID 337727Notes

Reaction equation

HRID 337727 reaction equation
C(OC(=O)[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([O:23][C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[CH:18][C:17]=1[F:35])(=[O:15])=[O:14])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:22][C:20]1[C:19]([O:23][C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]2[N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[CH:18][C:17]([F:35])=[C:16]([S:13]([NH:7][C:8]2[N:9]=[CH:10][S:11][CH:12]=2)(=[O:15])=[O:14])[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89962730Tert-butyl[(5-chloro-2-fluoro-4-{[(1S*,2R*)-2-(1H-imidazol-1-yl)cyclohexyl]oxy}phenyl)sulfonyl](1,3-thiazol-4-yl)carbamic acid

Product 1

HCID 899631915-Chloro-2-fluoro-4-{[(1S*,2S*)-2-(1H-imidazol-1-yl)cyclohexyl]oxy}-N-(1,3-thiazol-4-yl)benzenesulfonamideYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the tert-butyl[(5-chloro-2-fluoro-4-{[(1S*,2R*)-2-(1H-imidazol-1-yl)cyclohexyl]oxy}phenyl)sulfonyl](1,3-thiazol-4-yl)carbamic acid (340 mg, 0.610 mmol) prepared in Example 13a, trifluoroacetic acid (5.0 mL) and dichloromethane (5.0 mL), to yield the title compound (292 mg, 67%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-e730eecfa62342ada4b0883b481b9bc0
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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