HCID 67281838, compound → HCID 136390989, compound

HRID 1616139Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([CH:17]2[NH:26][C:25](=[O:27])[C:24]3[C:19](=[CH:20][C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:23]=3)[NH:18]2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[NH:26][C:25](=[O:27])[C:24]3[C:19](=[CH:20][C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:23]=3)[N:18]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 2-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (60 mg, 0.1 mmol) in chloroform (1.5 mL) was added manganese (IV) oxide (81.4 mg, 0.94 mmol). The reaction mixture was heated to 70° C. and stirred for 3 h. The mixture was cooled to rt, the solid filtered and washed with MeOH to afford methyl 2-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (60 mg, quant). LC-MS: (FA) ES+ 331.

Workup

temperatureThe mixture was cooled to rt
filtrationthe solid filtered
washwashed with MeOH

Sources & evidence

ORD record: ord-1147aebec7d347cbbde0c712fa1d9e1a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765773B2

Reaction notes

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