Sodium hydride → 4-{[(1S*,2R*)-4,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(2,4-dimethoxybenzyl)-2,6-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 337941Notes

Reaction equation

HRID 337941 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[C:15]([F:16])=[CH:14][C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].[F:31][C:32]1([F:45])[CH2:37][CH2:36][C@H:35]([OH:38])[C@@H:34]([C:39]2[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=2)[CH2:33]1.[H-].[Na+]>CN(C=O)C>[F:45][C:32]1([F:31])[CH2:37][CH2:36][C@H:35]([O:38][C:13]2[CH:14]=[C:15]([F:16])[C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:3]=3[O:2][CH3:1])[C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)(=[O:8])=[O:9])=[C:11]([F:18])[CH:12]=2)[C@@H:34]([C:39]2[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=2)[CH2:33]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 89963011HCID 89963011, compoundHCID 89963776N-(2,4-dimethoxybenzyl)-2,4,6-trifluoro-N-(pyrimidin-4-yl)benzenesulfonamide

Product 1

HCID 899629494-{[(1S*,2R*)-4,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(2,4-dimethoxybenzyl)-2,6-difluoro-N-(pyrimidin-4-yl)benzenesulfonamideYield 48.3%

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)-2,4,6-trifluoro-N-(pyrimidin-4-yl)benzenesulfonamide (150 mg, 0.34 mmol) prepared in Example 27a, the (1S*,2R*)-4,4-difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanol (61.6 mg, 0.28 mmol) prepared in Example 88 g, sodium hydride (63%; 21.7 mg, 0.57 mmol) and DMF (2.0 mL), to yield the title compound (85.9 mg, 47%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-b4d4938765db472bb78acb53e5041737
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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