Potassium Carbonate → 1-(2-hydroxy-4-{3-[1-(methoxyimino)ethyl]phenyl}-4-methyl-2-trifluoromethyl-pentyl)-1H-quinolin-4-one

HRID 2106035Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([C:10]([CH3:31])([CH3:30])[CH2:11][C:12]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:13][N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[CH:16]=[CH:15]2)[CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:39][O:40][NH2:41]>CO>[OH:29][C:12]([C:25]([F:26])([F:27])[F:28])([CH2:11][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[N:41][O:40][CH3:39])[CH3:2])[CH:5]=1)([CH3:30])[CH3:31])[CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[CH:16]=[CH:15]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1-H-quinolin-4-one (55 mg, 0.12 mmol), potassium carbonate (72 mg, 0.52 mmol), and methoxyamine hydrochloride (42 mg, 0.51 mmol) in 1 mL of methanol was heated at 65° C. for 3 hours, cooled to room temperature, and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography to afford 1-(2-hydroxy-4-{3-[1-(methoxyimino)ethyl]phenyl}-4-methyl-2-trifluoromethyl-pentyl)-1H-quinolin-4-one. Yield: 48 mg.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
additionThe residue was diluted with water
extractionextracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-d00d0da39b0c4797bd411b3dce67b49c
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579469B2

Reaction notes

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