Cyclopropyl methyl ketone → HCID 22648082, compound

HRID 394158Notes

Reaction equation

HRID 394158 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:33])[N:13]2[C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32].[CH:34]1([C:37](=O)[CH3:38])[CH2:36][CH2:35]1.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([O:18][CH:19]2[CH2:20][CH2:21][N:22]([CH:37]([CH:34]3[CH2:36][CH2:35]3)[CH3:38])[CH2:23][CH2:24]2)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:33])[N:13]2[C:25]1[C:26]([Cl:32])=[CH:27][CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketone2×HCID 5003444Sodium cyanoborohydrideHCID 22648061HCID 22648061, compound

Product 1

HCID 22648082HCID 22648082, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8.8 mg of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(piperidin-4-yloxy)quinolin-2(1H)-one in 0.9 mL of MeOH was added 0.1 mL of 1-cyclopropylethanone, then 6.5 mg of sodium cyanoborohydride. The mixture was stirred 4 d at rt. Another 0.5 mL of 1-cyclopropylethanone was added and the mixture was heated to reflux overnight, then concentrated and purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH to yield the title compound. Mass spectrum (ESI) 567 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. custompurified by preparative thin-layer chromatography
  5. washeluting with 95:5 CH2Cl2-2M NH3 in MeOH

Sources & evidence

ORD record
ord-713111a01cb94a8aac2d7b9abc646b97
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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