Pyridine → methyl 3-[8-(aminocarbonyl)-6-iodo-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

HRID 641966Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=O)[CH:11]=1)[N:8]=[CH:7][N:6]([C:15]1[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:16]=1[CH3:25])[C:5]2=[O:26].[N:27]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O1CCOCC1>[NH2:27][C:12]([C:10]1[CH:11]=[C:2]([I:1])[CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][N:6]([C:15]1[CH:20]=[C:19]([CH:18]=[CH:17][C:16]=1[CH3:25])[C:21]([O:23][CH3:24])=[O:22])[C:5]2=[O:26])=[O:14]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 6-iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid (2.4 g) in 1,4-dioxane (50 ml) was added pyridine (0.42 ml), di-tert-butyl dicarbonate (1.47 g) and NH4HCO3 (0.53 g). The reaction mixture was stirred at 40° C. for 18 hours and concentrated. The resultant white solid was washed with methanol and dried to yield methyl 3-[8-(aminocarbonyl)-6-iodo-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate as a white solid (2.28 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.85 (s, 3H), 7.61 (d, 1H), 8.03 (m, 3H), 8.52 (s, 1H), 8.60 (m, 1H), 8.70 (m, 1H), 9.33 (s, 1H); Mass Spectrum: M+H+ 464.

Workup

concentrationconcentrated
washThe resultant white solid was washed with methanol
customdried

Sources & evidence

ORD record: ord-4e71d9ad66ac4eec858d6cb721ae9d2e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696215B2

Reaction notes

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