HCID 86712701, compound → HCID 86712702, compound

HRID 1779058Notes

Reaction equation

HRID 1779058 reaction equation
[CH3:1][O:2][C:3](=[O:47])[CH2:4][C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:6]=1[C:15]#[C:16][C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[C:19]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]3)=[CH:30][CH:29]=2)[N:18]=1>CCOC(C)=O.C(N(CC)CC)C.[Pd]>[CH3:1][O:2][C:3](=[O:47])[CH2:4][C:5]1[C:10]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:15][CH2:16][C:17]1[C:22]([C:23]([F:25])([F:26])[F:24])=[CH:21][N:20]=[C:19]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:35][CH2:36][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38][CH2:39]3)=[CH:30][CH:29]=2)[N:18]=1

Participants

5

Reactant 1

HCID 86712701HCID 86712701, compound

Product 1

HCID 86712702HCID 86712702, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of tert-butyl 4-(4-((4-((2-(2-methoxy-2-oxoethyl)-3-(trifluoromethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A94) (0.127 g, 0.192 mmol) and 10% Pd/C (53% water; 0.234 g) in EtOAc (4.0 mL) and triethylamine (0.2 mL) was stirred under a hydrogen atmosphere for 20 hours. The resulting mixture was filtered through Celite and the filtrate concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15-30% EtOAc in petroleum benzine 40-60° C.) to give the title compound A95 (0.106 g, 83%); 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 7.56 (m, 3H), 7.46 (d, J=7.3 Hz, 1H), 7.36 (m, 2H), 7.21 (d, J=8.5 Hz, 2H), 4.25 (m, 2H), 3.98 (s, 2H), 3.68 (s, 3H), 3.11 (m, 4H), 2.81 (m, 2H), 2.64 (m, 1H), 1.83 (m, 2H), 1.62 (m, 2H), 1.49 (s, 9H). LCMS-A: rt 7.19 min; m/z 665.1 [M−H]−.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (15-30% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-8c63901817874243b3dae9b409eded4c
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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