N-(3-chloro-4-(difluoromethoxy)phenyl)-5-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)pyrimidin-2-amine → HCID 86679772, compound

HRID 77482Notes

Reaction equation

HRID 77482 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:27](=[CH:28][CH:29]=3)[N:26]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)[N: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:27](=[CH:28][CH:29]=3)[N:26]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)[N:25]=[CH:24]4)=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([F:10])[F:11]

Participants

4

Reactant 1

HCID 86679773N-(3-chloro-4-(difluoromethoxy)phenyl)-5-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)pyrimidin-2-amine

Product 1

HCID 86679772HCID 86679772, compoundYield 159.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-chloro-4-(difluoromethoxy)phenyl)-5-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)pyrimidin-2-amine (0.10 g, 0.201 mmol) in ethyl acetate (10 mL) was added Pd/C (0.214 g, 2.008 mmol). The reaction mixture was stirred at room temperature under hydrogen for 12 h. The reaction mixture was filtered through celite and the filtrate was concentrated to give N-(3-chloro-4-(difluoromethoxy)phenyl)-5-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)pyrimidin-2-amine (0.16 g, 80%). LCMS (ES-API), RT: 2.21 m/z 500.2 (M+H).

Workup

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

Sources & evidence

ORD record
ord-2d192114dc14401e971990fbec148079
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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