Ethyl Acetate → 5-[3-[(1S)-2-(Difluoromethoxy)-1-methylethoxy]-5-[[(5-methyl-2-pyrazinyl)amino]carbonyl]phenoxy]-N,N-dimethyl-2-pyrazinecarboxamide

HRID 2425479Notes

Reaction equation

[F:1][CH:2]([F:25])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([OH:24])[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[CH3:6].Cl[C:27]1[N:28]=[CH:29][C:30]([C:33]([N:35]([CH3:37])[CH3:36])=[O:34])=[N:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[F:25][CH:2]([F:1])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:23]=[C:22]([CH:21]=[C:10]([C:11](=[O:12])[NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:9]=1)[O:24][C:27]1[N:28]=[CH:29][C:30]([C:33]([N:35]([CH3:37])[CH3:36])=[O:34])=[N:31][CH:32]=1)[CH3:6]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-N-(5-methylpyrazin-2-yl)benzamide (0.19 g, 0.54 mmol), 5-chloro-N,N-dimethyl-pyrazine-2-carboxamide (100 mg, 0.54 mmol) and potassium carbonate (149 mg, 1.08 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 140° C. for 5 hours and the mixture reduced in vacuo. Ethyl acetate (50 mL) was added and the mixture washed with water (50 mL), brine (50 mL), dried (MgSO4), and reduced in vacuo. The crude residue was chromatographed on silica, eluting with 0-5% methanol in DCM, to give the desired compound (150 mg).

Workup

washthe mixture washed with water (50 mL), brine (50 mL)
dry with materialdried (MgSO4)
customThe crude residue was chromatographed on silica
washeluting with 0-5% methanol in DCM

Sources & evidence

ORD record: ord-9fc922de47f345a5848291c037868938
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964725B2

Reaction notes

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