HCID 71225437, compound → Tert-butyl 4-(4-((4-(3-carbamoylphenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate

HRID 705756Notes

Reaction equation

HRID 705756 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:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[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>[C:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][CH2:11][C:12]1[C:17]([C:18]([F:21])([F:19])[F:20])=[CH:16][N:15]=[C:14]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:30][CH2:31][N:32]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:33][CH2:34]3)=[CH:25][C:24]=2[O:42][CH3:43])[N:13]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 71225437HCID 71225437, compound

Product 1

HCID 68283219Tert-butyl 4-(4-((4-(3-carbamoylphenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-methoxyphenyl)piperidine-1-carboxylate

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% acetaneipetroleum 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% acetaneipetroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-a7c5d77012274d92832677c2bc253f7d
Source dataset
uspto-grants-2015_11
Patent number
US09174946B2

Reaction notes

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