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

HRID 394087Notes

Reaction equation

HRID 394087 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]([C:19]3[CH2:28][CH2:27][C:22]4([O:26][CH2:25][CH2:24][O:23]4)[CH2:21][CH:20]=3)[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:36]>C(OCC)(=O)C.[Pt]=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[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([O:26][CH2:25][CH2:24][O:23]4)[CH2:21][CH2:20]3)[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:36]

Participants

4

Reactant 1

HCID 226480661-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-7-ene-8-yl)-3,4-dihydro-2(1H)-quinazolinone2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 1-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-7-ene-8-yl)-3,4-dihydro-2(1H)-quinazolinone (818.8 mg, 1.51 mmol) (INTERMEDIATE 71) in ethyl acetate (25 mL) under a nitrogen atmosphere was added platinum oxide (Adam's catalyst, 164 mg). The reaction mixture was purged with H2 (via balloon) and stirred for 2 hours. Proton NMR analysis of an aliquot showed incomplete reduction. An additional 82 mg of PtO2 was added and the solution stirred under a H2 atmosphere for another hour. The reaction mixture was filtered over Celite, rinsed with 10% MeOH in DCM and concentrated. The crude material purified by silica gel chromatography eluting with 1% MeOH in DCM to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-8-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data δ 1.61 (m, 4H), 1.78 (m, 4H), 2.38 (m, 1H), 3.92 (m, 4H).

Workup

  1. customThe reaction mixture was purged with H2 (via balloon)
  2. additionAn additional 82 mg of PtO2 was added
  3. stirringthe solution stirred under a H2 atmosphere for another hour
  4. filtrationThe reaction mixture was filtered over Celite
  5. washrinsed with 10% MeOH in DCM
  6. concentrationconcentrated
  7. customThe crude material purified by silica gel chromatography
  8. washeluting with 1% MeOH in DCM

Sources & evidence

ORD record
ord-b015572b65a64129ad07f6636f0687dd
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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