Ethanol → HCID 59405026, compound

HRID 1892190Notes

Reaction equation

HRID 1892190 reaction equation
[CH3:1][N:2]([CH3:37])[CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([NH:16][C:17]2[N:18]=[CH:19][C:20]3[CH2:21][C:22](=[O:36])[NH:23][C:24]4[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:25]=4[C:26]=3[N:27]=2)[C:9]([C:12]([F:15])([F:14])[F:13])=[N:10][CH:11]=1.CCO>[Ni].C1COCC1>[CH3:37][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH:16][C:17]2[N:18]=[CH:19][C:20]3[CH2:21][C:22](=[O:36])[NH:23][C:24]4[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[CH:28][C:25]=4[C:26]=3[N:27]=2)[C:9]([C:12]([F:15])([F:14])[F:13])=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 59405009HCID 59405009, compound

Product 1

HCID 59405026HCID 59405026, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask were added 2-{[5-[3-(dimethylamino)prop-1-yn-1-yl]-2-(trifluoromethyl)pyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.042 g, 0.081 mmol), EtOH (5 mL), THF (1 mL), and Raney nickel (20 mg). The resulting mixture was allowed to stir under a hydrogen balloon overnight. The mixture was filtered through celite and the filtrate was concentrated. The residue was purified by column chromatography to give 2-{[5-[3-(dimethylamino)propyl]-2-(trifluoromethyl)pyridin-3-yl]amino}-9-(trifluoromethyl)-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.033 g, 78%) as a solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2681aa7b2f09440f8aee40201f0e57f1
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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