HCID 86712638, compound → HCID 86712639, compound

HRID 1778969Notes

Reaction equation

HRID 1778969 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([C:23]#[C:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:20]([C:36]([F:39])([F:38])[F:37])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.CCN(CC)CC.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[N:22]=[C:21]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:20]([C:36]([F:38])([F:39])[F:37])=[CH:19][N:18]=2)=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 86712638HCID 86712638, compound

Product 1

HCID 86712639HCID 86712639, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 10% Pd/C (200 mg) and methyl 2-(2-((2-((4-(((tert-butoxycarbonyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)acetate (A13) (412 mg, 0.762 mmol) in DMF (5 mL) and Et3N (1 mL) was stirred under a hydrogen atmosphere at room temperature for 16 h. The resulting mixture was filtered through Celite, washing with EtOAc (200 mL) then the combined filtrates were evaporated in vacuo to give the title compound A14 as a white solid (306 mg, 74%); 1H NMR (400 MHz, d6-DMSO) δ 10.19 (s, 1H), 8.68 (s, 1H), 7.68 (d, J=8.5 Hz, 2H), 7.34 (t, J=6.0 Hz, 1H), 7.27-7.16 (m, 6H), 4.09 (d, J=6.0 Hz, 2H), 3.76 (s, 2H), 3.59 (s, 3H), 3.11-2.95 (m, 4H), 1.40 (s, 9H). LCMS-A: rt 6.637 min; m/z 545 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. washwashing with EtOAc (200 mL)
  3. customthe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-d1521ff2fd3e4c39a346d99a35c44be8
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

Loading…