Ethyl Acetate → HCID 15949593, compound

HRID 548715Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([O:17][C@@H:18]([CH3:22])[CH2:19][O:20][CH3:21])[CH:16]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=1)=[O:6].F[C:24]1[CH:37]=[CH:36][C:27]2[C:28](=[O:35])[N:29]([CH3:34])[C:30]([CH3:33])([CH3:32])[O:31][C:26]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[CH3:22][C@H:18]([O:17][C:15]1[CH:14]=[C:4]([CH:3]=[C:2]([O:1][C:24]2[CH:37]=[CH:36][C:27]3[C:28](=[O:35])[N:29]([CH3:34])[C:30]([CH3:33])([CH3:32])[O:31][C:26]=3[CH:25]=2)[CH:16]=1)[C:5]([NH:7][C:8]1[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=1)=[O:6])[CH2:19][O:20][CH3:21]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (0.25 g, 0.82 mmol), 7-fluoro-2,2,3-trimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one (172 mg, 0.82 mmol) and potassium carbonate (226 mg, 1.64 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 160° C. for 12 hours. The mixture was reduced in vacuo and ethyl acetate (50 mL) added. The mixture was washed with water (50 mL), brine (50 mL), dried (MgSO4), and reduced in vacuo to give a brown oil which was chromatographed on silica, eluting with 0-10% methanol in DCM, to give the desired compound as a white foam (122 mg).

Workup

additionadded
washThe mixture was washed with water (50 mL), brine (50 mL)
dry with materialdried (MgSO4)
customto give a brown oil which
customwas chromatographed on silica
washeluting with 0-10% methanol in DCM

Sources & evidence

ORD record: ord-e226c6586c7d490388e5675892cc3427
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943607B2

Reaction notes

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