HCID 17904941, compound → 6-Acetoxy-7-methoxy-4-[2-methyl-5-(2-morpholinopyridine-4-carboxamido)anilino]quinazoline Dihydrochloride

HRID 2084017Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[ClH:24].[C:25]([O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][N:33]=[C:32]2[Cl:41])(=[O:27])[CH3:26]>C(O)(C)C>[ClH:41].[ClH:24].[C:25]([O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][N:33]=[C:32]2[NH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8])(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide (178 mg), 6-acetoxy-4-chloro-7-methoxyquinazoline hydrochloride (150 mg) and isopropanol (5 ml) was stirred and heated to 85° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature and the solid was isolated and washed in turn with isopropanol (5 ml) and isohexane (2×5 ml). There was thus obtained the title compound (249 mg, 80%); NMR: 2.17 (s, 3H), 2.38 (s, 3H), 3.56 (m, 4H), 3.72 (m, 4H), 4.0 (s, 3H), 7.16 (m, 1H), 7.37 (m, 2H), 7.52 (s, 1H), 7.68 (m, 1H), 7.87 (m, 1H), 8.24 (m, 1H), 8.67 (s, 1H), 8.8 (s, 1H), 10.6 (s, 1H), 11.50 (s, 1H); m/s: M+H+ 529.

Workup

temperatureto cool to ambient temperature
customthe solid was isolated
washwashed in turn with isopropanol (5 ml) and isohexane (2×5 ml)

Sources & evidence

ORD record: ord-4ebd3b192c98400c8213269fb995b7d1
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716847B2

Reaction notes

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