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

HRID 337725Notes

Reaction equation

HRID 337725 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[CH2:28][CH2:27][CH2:26][C@@H:25]2[C:29]2[N:33]([CH2:34][CH3:35])[N:32]=[CH:31][CH:30]=2)=[CH:18][C:17]=1[F:36])(=[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[CH2:28][CH2:27][CH2:26][C@@H:25]2[C:29]2[N:33]([CH2:34][CH3:35])[N:32]=[CH:31][CH:30]=2)=[CH:18][C:17]([F:36])=[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 89963428Tert-butyl[(5-chloro-2-fluoro-4-{[(1S*,2R*)-2-(1-ethyl-1H-pyrazol-5-yl)cyclopentyl]oxy}phenyl) sulfonyl](1,3-thiazol-4-yl)carbamic acid

Product 1

HCID 899632685-Chloro-2-fluoro-4-{[(1S*,2R*)-2-(1-ethyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(1,3-thiazol-4-yl)benzenesulfonamideYield 69.8%

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-(1-ethyl-1H-pyrazol-5-yl)cyclopentyl]oxy}phenyl)sulfonyl](1,3-thiazol-4-yl)carbamic acid (125 mg, 0.213 mmol) prepared in Example 12b, trifluoroacetic acid (1.0 mL) and dichloromethane (1.0 mL), to yield the title compound (70.0 mg, 68%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-3bfe0b892588405bacc6f521f0414dcc
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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