Potassium Hydroxide → HCID 22647919, compound

HRID 394127Notes

Reaction equation

HRID 394127 reaction equation
[I-].[CH3:2][S+](C)C.[OH-].[K+].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[N:16]1[C:25]2[C:20](=[C:21]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[CH:22]=[C:23]([CH:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)[CH:24]=2)[CH2:19][N:18]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[C:17]1=[O:49]>CC#N.O.CS(C)=O.C(Cl)Cl>[Cl:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:21]1[CH:22]=[C:23]([CH:26]2[CH2:31][CH2:30][C:29]3([O:32][CH2:2]3)[CH2:28][CH2:27]2)[CH:24]=[C:25]2[C:20]=1[CH2:19][N:18]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1)[C:17](=[O:49])[N:16]2[C:10]1[C:11]([Cl:15])=[CH:12][CH:13]=[CH:14][C:9]=1[Cl:8]

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 75127Trimethylsulfonium iodideHCID 22647965HCID 22647965, compound2×

Product 1

HCID 22647919HCID 22647919, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of trimethylsulfonium iodide (20 mg, 0.096 mmol) in CH3CN (0.3 mL) was added one drop of H2O followed KOH (s) (22 mg, 0.384 mmol). This mixture was heated at 60° C. for 10 min, then added 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-(4-oxocyclohexyl)-3,4-dihydroquinazolin-2(1H)-one (INTERMEDIATE 76) (40 mg, 0.064 mmol) in CH3CN (0.3 mL) and DMSO (0.2 mL) slowly. The reaction mixture was heated another 3.5 h, cooled to RT and diluted with CH2Cl2. It was washed with H2O followed by brine then dried over Na2SO4. After removal of the solvent, the crude product was purified by preparative thin layer chromatography eluting with 1:3 acetone:hexane to give the title compound as a mixture of diastereomers. Mass spectrum (ESI): 633.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated another 3.5 h
  2. temperaturecooled to RT
  3. washIt was washed with H2O
  4. dry with materialthen dried over Na2SO4
  5. customAfter removal of the solvent
  6. customthe crude product was purified by preparative thin layer chromatography
  7. washeluting with 1:3 acetone

Sources & evidence

ORD record
ord-54adc5dbec01489f8a1330188524b5b7
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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