1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-8-yl)-3,4-dihydro-2(1H)-quinazolinone → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone

HRID 394088Notes

Reaction equation

HRID 394088 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH:15]=[C:16]([CH:19]3[CH2:28][CH2:27][C:22]4(OCC[O:23]4)[CH2:21][CH2:20]3)[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:36]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH:15]=[C:16]([CH:19]3[CH2:20][CH2:21][C:22](=[O:23])[CH2:27][CH2:28]3)[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:36]

Participants

3

Reactant 1

HCID 226479511-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-8-yl)-3,4-dihydro-2(1H)-quinazolinone2×

Product 1

HCID 226480091-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-8-yl)-3,4-dihydro-2(1H)-quinazolinone (248 mg, 0.456 mmol) (INTERMEDIATE 72) in acetone (12 mL) was added Amberlyst-15 (130 mg). The mixture was stirred at RT for 6 hours at which time the reaction mixture became homogeneous. The solution was filtered and the solvent concentrated. The crude material was purified by silica gel chromatography eluting with 1:4 acetone:hexanes followed by 1:3 acetone:hexanes to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data δ 1.78 (m, 2H), 2.14 (m, 2H), 2.4 (m, 4H) 2.86 (m, 1H). MS(ES) 499 (M+H); LC 1: 3.19 min.

Workup

  1. additionwas added Amberlyst-15 (130 mg)
  2. filtrationThe solution was filtered
  3. concentrationthe solvent concentrated
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with 1:4 acetone

Sources & evidence

ORD record
ord-9fde97a05dfd4d2bb3f1f0a1a92d5099
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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