HCID 59519059, compound → HCID 59519057, compound

HRID 1161854Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[N:6]([CH2:19][C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:5]2=[O:27]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[N:6]([CH2:19][C:20]([NH:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:5]2=[O:27]

Participants

Conditions

Temperature: 70 °C

Procedure

In a capped 20 mL scintillation vial, a mixture of 2-[6-bromo-2-(3-chlorophenyl)-4-oxo-1,4-dihydro-2H-quinazolin-3-yl]-N-tert-butylacetamide (0.51 g, 1.13 mmol) and manganese(IV) dioxide (0.44 g, 5.10 mmol) in chloroform (10 mL) was heated at 70° C. for 3 h. The black suspension was cooled to room temperature, filtered through a pad of celite and concentrated in vacuo to provide 2-[6-bromo-2-(3-chlorophenyl)-4-oxo-4H-quinazolin-3-yl]-N-tert-butylacetamide (INTERMEDIATE VI.1) (0.51 g, 1.13 mmol, 100%) as a white solid. Data for 2-[6-bromo-2-(3-chlorophenyl)-4-oxo-4H-quinazolin-3-yl]-N-tert-butylacetamide (INTERMEDIATE VI.1): 1H NMR (300 MHz, CDCl3): δ 9.44 (d, 1H), 7.86 (dd, 1H), 7.65-7.54 (m, 2H), 7.53-7.4 (m, 3H), 5.47 (s, 1H), 4.46 (s, 2H), 1.34 (s, 9H) ppm; MS (ESI) m/z: 448/450 ([M+H]+).

Workup

temperatureThe black suspension was cooled to room temperature
filtrationfiltered through a pad of celite
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-92019c3da7684f82b87fb6ffbfee6ae9
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820649B2

Reaction notes

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