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 2425494Notes

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-3a0234fb520e4e96a5884fa972bf0e15
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964725B2

Reaction notes

Loading…