HCID 71225437, compound → 3-(2-(2-((2-Methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)benzamide

HRID 2272423Notes

Reaction equation

HRID 2272423 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]#[C:11][C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]4)=[CH:25][C:24]=3[O:42][CH3:43])[N:13]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2]>[Pd].CN(C=O)C>[CH3:43][O:42][C:24]1[CH:25]=[C:26]([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:27]=[CH:28][C:23]=1[NH:22][C:14]1[N:13]=[C:12]([CH2:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:1]([NH2:2])=[O:3])[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][N:15]=1

Participants

4

Reactant 1

HCID 71225437HCID 71225437, compound

Product 1

HCID 601621213-(2-(2-((2-Methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 4-(4-((4-((3-carbamoylphenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate (I35) (0.073 g, 0.12 mmol) and 10% palladium on activated carbon (0.042 g) in DMF (3 mL) was stirred under a hydrogen atmosphere for 20 hours. The resulting mixture was filtered and filtrate evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel (20-100% acetone/petroleum benzine 40-60° C.) to give the title compound (I36) (0.070 g, 95%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customfiltrate evaporated to dryness under reduced pressure
  3. customThe residue was chromatographed on silica gel (20-100% acetone/petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-baec03a9d6034714a9b7151f06ee9b0c
Source dataset
uspto-grants-2015_09
Patent number
US09120761B2

Reaction notes

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