Ethyl Acetate → 5-[3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-[(1-methylpyrazol-3-yl) carbamoyl]phenoxy]-N,N-dimethyl-pyrazine-2-carboxamide

HRID 2241947Notes

Reaction equation

[F:1][CH:2]([F:24])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([OH:23])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12])[CH3:6].Cl[C:26]1[N:27]=[CH:28][C:29]([C:32]([N:34]([CH3:36])[CH3:35])=[O:33])=[N:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[F:24][CH:2]([F:1])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:22]=[C:21]([CH:20]=[C:10]([C:11](=[O:12])[NH:13][C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)[CH:9]=1)[O:23][C:26]1[N:27]=[CH:28][C:29]([C:32]([N:34]([CH3:36])[CH3:35])=[O:33])=[N:30][CH:31]=1)[CH3:6]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-N-(1-methylpyrazol-3-yl)benzamide (0.1 g, 0.29 mmol), 5-chloro-N,N-dimethyl-pyrazine-2-carboxamide (66 mg, 0.35 mmol) and potassium carbonate (81 mg, 0.59 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 160° C. for 6 hours. The resulting mixture was reduced in vacuo and ethyl acetate (50 mL) added. The organics were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and reduced in vacuo. The residue was chromatographed on silica, eluting with 10-100% ethyl acetate in isohexane to give the desired compound (52 mg).

Workup

additionadded
washThe organics were washed with water (50 mL), brine (50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customThe residue was chromatographed on silica
washeluting with 10-100% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-3fc2a28f6d054f0a9b43513b17f8742a
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671060B2

Reaction notes

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