(RS)-S-(4-{[4-{[(1R,2R)-2-(Benzyloxy)-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-cyclopropyl-N-(trifluoroacetyl)sulfoximide → (RS)-S-cyclopropyl-S-(4-{[4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-N-(trifluoroacetyl)sulphoximide

HRID 2199516Notes

Reaction equation

HRID 2199516 reaction equation
C([O:8][C@H:9]([CH3:42])[C@H:10]([O:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH:39]3[CH2:41][CH2:40]3)(=[N:32][C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])=[O:31])=[CH:26][CH:25]=2)[N:14]=1)[CH3:11])C1C=CC=CC=1>C(O)C.[Pd]>[CH:39]1([S:30]([C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:15]3[N:14]=[C:13]([O:12][C@H:10]([CH3:11])[C@H:9]([OH:8])[CH3:42])[C:18]([C:19]([F:21])([F:22])[F:20])=[CH:17][N:16]=3)=[CH:29][CH:28]=2)(=[N:32][C:33](=[O:38])[C:34]([F:36])([F:35])[F:37])=[O:31])[CH2:41][CH2:40]1

Participants

4

Reactant 1

HCID 58533490(RS)-S-(4-{[4-{[(1R,2R)-2-(Benzyloxy)-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-cyclopropyl-N-(trifluoroacetyl)sulfoximide

Product 1

HCID 58533494(RS)-S-cyclopropyl-S-(4-{[4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-N-(trifluoroacetyl)sulphoximideYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (RS)—S-(4-{[4-{[(1R,2R)-2-(benzyloxy)-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-S-cyclopropyl-N-(trifluoroacetyl)sulphoximide in ethanol was admixed with palladium on carbon (10%) and hydrogenated under atmospheric pressure at room temperature. The mixture was filtered and concentrated by evaporation (yield: 79%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by evaporation (yield: 79%)

Sources & evidence

ORD record
ord-7b226e733ab14840b41e7ab4f7f1e67f
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

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