Sodium hydride → N-(2,4-Dimethoxybenzyl)-4-{[(1S*,2R*)-2-(1-ethyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-2,5-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 337773Notes

Reaction equation

HRID 337773 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].[CH2:31]([N:33]1[C:37]([C@H:38]2[CH2:42][CH2:41][CH2:40][C@@H:39]2[OH:43])=[CH:36][CH:35]=[N:34]1)[CH3:32].[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][N:6]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:43][C@H:39]2[CH2:40][CH2:41][CH2:42][C@@H:38]2[C:37]2[N:33]([CH2:31][CH3:32])[N:34]=[CH:35][CH:36]=2)=[CH:12][C:11]=1[F:18])(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 89556048N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(pyrimidin-4-yl)benzenesulfonamideHCID 89962858(1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclopentanol

Product 1

HCID 89963510N-(2,4-Dimethoxybenzyl)-4-{[(1S*,2R*)-2-(1-ethyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-2,5-difluoro-N-(pyrimidin-4-yl)benzenesulfonamideYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 1a by using the N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(pyrimidin-4-yl)benzenesulfonamide (200 mg, 0.455 mmol) prepared in Example 14b, (1S*,2R*)-2-(1-ethyl-1H-pyrazol-5-yl)cyclopentanol (78.0 mg, 0.432 mmol) prepared in Example 37a, sodium hydride (63%; 24.7 mg, 0.648 mmol) and DMF (2.0 mL), to yield the title compound (210 mg, 81%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-95fe2113e90b4214b15fd2e55c430b03
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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