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

HRID 337943Notes

Reaction equation

HRID 337943 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1)[S:7]([C:10]1[CH:15]=[CH:14][C:13](F)=[CH:12][C:11]=1[F:17])(=[O:9])=[O:8].[F:30][C:31]1([F:44])[CH2:36][CH2:35][C@H:34]([OH:37])[C@@H:33]([C:38]2[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=2)[CH2:32]1.[H-].[Na+]>CN(C=O)C>[F:44][C:31]1([F:30])[CH2:36][CH2:35][C@H:34]([O:37][C:13]2[CH:14]=[CH:15][C:10]([S:7]([N:6]([CH2:5][C:4]3[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:3]=3[O:2][CH3:1])[C:18]3[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)(=[O:9])=[O:8])=[C:11]([F:17])[CH:12]=2)[C@@H:33]([C:38]2[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=2)[CH2:32]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 89962746N-(2,4-Dimethoxybenzyl)-2,4-difluoro-N-(pyrimidin-4-yl)benzenesulfonamideHCID 89963011(1S*,2R*)-4,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanol

Product 1

HCID 899631074-{[(1S*,2R*)-4,4-Difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(pyrimidin-4-yl)benzenesulfonamideYield 39.1%

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-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (167 mg, 0.40 mmol) prepared in Example 29a, the (1S*,2R*)-4,4-difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanol (71.5 mg, 0.33 mmol) prepared in Example 88 g, sodium hydride (63%; 25.2 mg, 0.66 mmol) and DMF (2.0 mL), to yield the title compound (79.7 mg, 39%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-4b7cd40138414d658f03958fd2883211
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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