Trifluoroacetic acid → 2,6-Difluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide

HRID 337906Notes

Reaction equation

HRID 337906 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[CH:5]=[C:4]([F:20])[C:3]=1[S:21]([N:24](CC1C=CC(OC)=CC=1OC)C(=O)OC(C)(C)C)(=[O:23])=[O:22].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[F:20][C:4]1[CH:5]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[CH:7]=[C:2]([F:1])[C:3]=1[S:21]([NH2:24])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 131732050t-butyl [(2,6-difluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}phenyl)sulfonyl](2,4-dimethoxybenzyl)carbamate

Product 1

HCID 899627312,6-Difluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamideYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the t-butyl [(2,6-difluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}phenyl)sulfonyl](2,4-dimethoxybenzyl)carbamate (0.74 g, 1.22 mmol) prepared in Example 111b, triethylsilane (0.97 mL), trifluoroacetic acid (1.2 mL) and dichloromethane (12 mL), to yield the title compound (232.9 mg, 54%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-e031961d83b640a1a650119538a8fec3
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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