N-(5-Amino-2-fluorophenyl)benzamide → 4-[3-Benzamido-4-fluoroanilino]-6,7,8-trimethoxyquinazoline Hydrochloride

HRID 2084012Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[Cl:19][C:20]1[C:29]2[C:24](=[C:25]([O:34][CH3:35])[C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1>C(O)(C)C>[ClH:19].[C:10]([NH:9][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[F:1])[NH:8][C:20]1[C:29]2[C:24](=[C:25]([O:34][CH3:35])[C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(2-Fluoro-5-aminophenyl)benzamide (276 mg) was added to a suspension of 4-chloro-6,7,8-trimethoxyquinazoline hydrochloride (293 mg) in isopropanol (8 ml) and the resultant mixture stirred and heated to 80° C. for 18 hours. The mixture was cooled to ambient temperature and the precipitated solid was isolated, washed with isopropanol then diethyl ether to yield the title compound as a solid (257 mg, 53%); NMR: 4.0 (s, 3H), 4.01 (s, 3H), 4.07 (s, 3H), 7.42 (t, 1H), 7.52 (m, 2H), 7.62 (m, 2H), 8.0 (m, 3H), 8.35 (s, 1H), 8.72 (s, 1H), 10.28 (s, 1H), 11.84 (broad s, 1H); m/s: M+H+ 449.

Workup

temperatureThe mixture was cooled to ambient temperature
customthe precipitated solid was isolated
washwashed with isopropanol

Sources & evidence

ORD record: ord-88d9077f425445289b57609bca5ea5bc
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716847B2

Reaction notes

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