tert-Butyl 4-(4-((4-((2-(1-(methoxycarbonyl)cyclobutyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate → tert-Butyl 4-(4-((4-(2-(1-(methoxycarbonyl)cyclobutyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

HRID 592452Notes

Reaction equation

HRID 592452 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[C:16][C:17]2[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[C:19]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]4)=[CH:30][CH:29]=3)[N:18]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]>CCOC(C)=O.CCN(CC)CC.[Pd]>[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][C:17]2[C:22]([C:23]([F:24])([F:26])[F:25])=[CH:21][N:20]=[C:19]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:45])([CH3:46])[CH3:44])=[O:41])[CH2:36][CH2:35]4)=[CH:30][CH:29]=3)[N:18]=2)[CH2:6][CH2:7][CH2:8]1)=[O:4]

Participants

5

Reactant 1

HCID 86712328tert-Butyl 4-(4-((4-((2-(1-(methoxycarbonyl)cyclobutyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Product 1

HCID 86712329tert-Butyl 4-(4-((4-(2-(1-(methoxycarbonyl)cyclobutyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C 10% (40 mg) was added to a solution of tert-butyl 4-(4-((4-((2-(1-(methoxycarbonyl)cyclobutyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate A54 (33 mg, 0.052 mmol) in EtOAc (10 mL) and Et3N (0.5 mL). The mixture was stirred under a hydrogen atmosphere overnight and then filtered through Celite. The filter cake was washed with EtOAc (50 mL) and the volatiles were removed in vacuo to give the title compound A55 as a yellow oil (31 mg, 93%). LCMS-A: rt 8.013 min; m/z 639.3 [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. washThe filter cake was washed with EtOAc (50 mL)
  3. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-33673ae54aa44d4a95aa3cb35c9f11c5
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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