HCID 86712682, compound → HCID 86712683, compound

HRID 1779035Notes

Reaction equation

HRID 1779035 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:25]=[C:24]([C:26]#[C:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:23]([C:39]([F:42])([F:41])[F:40])=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[CH2:9][CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:25]=[C:24]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:23]([C:39]([F:41])([F:42])[F:40])=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[CH2:9][CH2:10][OH:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86712682HCID 86712682, compound

Product 1

HCID 86712683HCID 86712683, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 2-(2-((2-((4-(((tert-butoxycarbonyl)(2-hydroxyethyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)acetate (A72) (0.589 g, 1.00 mmol) and 10% Pd/C (0.300 g) in EtOAc (13 mL) was stirred under a hydrogen atmosphere for 18 hours. A further portion of 10% Pd/C (0.300 g) was added and the resulting mixture stirred under a hydrogen atmosphere for 20 hours. The resulting mixture was filtered through a pad of Celite, washing with EtOAc and the filtrate concentrated in vacuo. The residue was purified using silica gel column chromatography (CombiFlash Rf, 24 g SiO2 Cartridge, 20-60% EtOAc in cyclohexane) to give the title compound A73 as a light yellow gum (0.443 g, 74%); 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 7.63 (d, J=8.3 Hz, 2H), 7.44 (s, 1H), 7.28-7.25 (m, 6H), 4.49 (brs, 2H), 3.77-3.70 (m, 7H), 3.42 (brs, 2H), 3.15-2.95 (m, 5H), 1.51 (s, 9H). LCMS-B: rt 8.469 min; m/z 589 [M+H]+.

Workup

  1. stirringthe resulting mixture stirred under a hydrogen atmosphere for 20 hours
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. washwashing with EtOAc
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-71c551a3a4cc400ab01486bbd358ab70
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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