Water → HCID 22736931, compound
Reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([F:16])=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=[O:4].C(N(CC)CC)C.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:32]2([OH:38])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:29]=[CH:30][CH:31]=1.O>CN(C=O)C>[F:16][C:6]1[C:5]([C:3](=[O:4])[CH2:2][N:35]2[CH2:34][CH2:33][C:32]([OH:38])([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH3:24])[CH:27]=3)[CH2:37][CH2:36]2)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:15])[NH:11]2Participants
Procedure
To a cooled solution of 6-(Bromoacetyl)-5-fluoro-3,4-dihydro-2(1H)-quinolinone (900 mg, 3.1 mmol) and triethylamine (0.88 ml, 6.3 mmol) in DMF (15 ml) was added dropwise a solution of 4-(3-Methoxyphenyl)-4-piperidinol (650 mg, 3.1 mmol) in DMF(15 ml) at 0° C. The mixture was stirred at room temperature for 3 h. The reaction mixture was added water and the resulting precipitate was filtered to afford 5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one (360 mg) as a brown solid. The filtrate was extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (dichloromethane/methanol=20/1) to afford 5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one as a yellow solid (270 mg). The obtained products were combined and used in the next step without further purification.
Workup
- filtrationthe resulting precipitate was filtered
Sources & evidence
- ORD record
- ord-e17aa17da24e49f4bcf6d2e1943409cf
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713490B2
Reaction notes
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