HCID 67259659, compound → HCID 67432945, compound

HRID 410687Notes

Reaction equation

HRID 410687 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22](/[CH:24]=[CH:25]/[C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 67259659HCID 67259659, compound

Product 1

HCID 67432945HCID 67432945, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-{(E)-2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethenyl}benzoate (100 mg, 0.201 mmol) was taken up in EtOAc (5 ml). Palladium on carbon (53.6 mg, 0.050 mmol) was added, and the reaction was purged with hydrogen (3×). The reaction was stirred under a hydrogen balloon at room temperature overnight. Upon complete conversion, the reaction was diluted with EtOAc and filtered through Celite. The filtrate was evaporated to dryness and purified by chromatography on silica gel (Biotage 25 g SNAP, 10-100% EtOAc/hexanes) to give methyl 4-{2-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}benzoate (82 mg, 0.164 mmol, 82% yield) as a colorless solid.

Workup

  1. customthe reaction was purged with hydrogen (3×)
  2. additionUpon complete conversion, the reaction was diluted with EtOAc
  3. filtrationfiltered through Celite
  4. customThe filtrate was evaporated to dryness
  5. custompurified by chromatography on silica gel (Biotage 25 g SNAP, 10-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-43fbc3a9020f4eb79fdf89dbb1cf9649
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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