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

HRID 2241933Notes

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-eb829c3e2b13428a93ff8df5bd4ab906
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671060B2

Reaction notes

Loading…