HCID 86679779, compound → HCID 86679778, compound

HRID 77486Notes

Reaction equation

HRID 77486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[N:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:26](=[O:39])[CH:25]=[CH:24]4)=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([F:11])[F:10]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[N:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])[C:26](=[O:39])[CH:25]=[CH:24]4)=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([F:11])[F:10]

Participants

4

Reactant 1

HCID 86679779HCID 86679779, compound

Product 1

HCID 86679778HCID 86679778, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 6-(2-(2-((3-chloro-4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (0.1 g, 0.175 mmol) in ethyl acetate (10 mL) was added Pd/C (0.186 g, 1.751 mmol) and the reaction mixture was stirred at room temperature under an atmosphere of H2 gas for 12 hours. The reaction mass was filtered through celite and the filtrate was concentrated to give 6-(2-(2-(3-chloro-4-(difluoromethoxy)phenylamino)pyrimidin-5-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (0.075 g, 74%). LCMS (ES-API), RT: 2.56 m/z 575.2 (M+H).

Workup

  1. filtrationThe reaction mass was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-70c58c58ebe249a9a99eff7eb9134fcc
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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