tert-Butyl 4-(4-((4-((5-fluoro-2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate → tert-Butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

HRID 1779014Notes

Reaction equation

HRID 1779014 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:40][C:41]([O:43][CH3:44])=[O:42])=[C:6]([C:8]#[C:9][C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][N:13]=[C:12]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH:27]4[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[N:11]=2)[CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:40][C:41]([O:43][CH3:44])=[O:42])=[C:6]([CH:7]=1)[CH2:8][CH2:9][C:10]1[C:15]([C:16]([F:18])([F:19])[F:17])=[CH:14][N:13]=[C:12]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([CH:27]3[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:31][CH2:32]3)=[CH:25][CH:26]=2)[N:11]=1

Participants

4

Reactant 1

HCID 86712665tert-Butyl 4-(4-((4-((5-fluoro-2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Product 1

HCID 86712666tert-Butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Pd/C 10% (0.100 g) and tert-butyl 4-(4-((4-((5-fluoro-2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A51) (0.158 g, 0.258 mmol) in EtOAc (20 mL) was stirred under a hydrogen atmosphere at room temperature overnight. The resulting mixture was filtered through a Celite plug, washing with EtOAc (100 mL) then the combined organic washings were evaporated in vacuo to yield the title compound A52 as a yellow oil (0.092 g, 58%); 1H NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 7.48 (d, J=8.5 Hz, 2H), 7.17-7.10 (m, 3H), 6.91-6.78 (m, 2H), 4.18 (s, 2H), 3.62 (s, 2H), 3.60 (s, 3H), 3.01 (s, 4H), 2.73 (t, J=11.9 Hz, 2H), 2.57 (tt, J=12.0, 3.4 Hz, 1H), 1.75 (d, J=12.8 Hz, 2H), 1.54 (qd, J=12.8, 4.2 Hz, 2H), 1.41 (s, 9H). LCMS-A: rt 6.727/6.998 min; m/z 617 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through a Celite plug
  2. washwashing with EtOAc (100 mL)
  3. customthe combined organic washings were evaporated in vacuo

Sources & evidence

ORD record
ord-d11b19d1403447e2bb0f7f9d44a8631b
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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