tert-Butyl 3-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate → tert-Butyl 3-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate

HRID 1779043Notes

Reaction equation

HRID 1779043 reaction equation
[CH3:1][O:2][C:3](=[O:41])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31]3)=[CH:26][CH:25]=2)[N:14]=1>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:41])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][C:13]1[C:18]([C:19]([F:21])([F:22])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]3[CH2:31][N:32]([C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:33]3)=[CH:26][CH:25]=2)[N:14]=1

Participants

4

Reactant 1

HCID 86712686tert-Butyl 3-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate

Product 1

HCID 86712687tert-Butyl 3-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of tert-butyl 3-(4-((4-((2-(2-methoxy-2-oxoethyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate (A79) (570 mg, 1.00 mmol) and 10% Pd/C (0.600 g) in EtOAc (13 mL) was stirred under a hydrogen atmosphere for 18 hours. The resulting mixture was filtered through a pad of Celite, washing with EtOAc and the filtrate concentrated in vacuo to give the title compound A80 as a light yellow foam (521 mg, 90%); 1H NMR (300 MHz, d6-DMSO) δ 8.56 (s, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.57 (s, 1H), 7.33 (d, J=8.5 Hz, 2H), 7.28-7.25 (m, 4H), 4.35 (t, J=8.7 Hz, 2H), 3.99 (dd, J=8.4, 6.7 Hz, 2H), 3.77 (m, 3H), 3.70 (brs, 3H), 3.13 (m, 4H), 1.44 (s, 9H). LCMS-B: rt 9.374 min; m/z 571 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. washwashing with EtOAc
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-c09c14275e424991bfa7a7d620b2e74d
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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