Hydrochloric Acid → 4-(4-Benzofuranylamino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline

HRID 495376Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 4chloro-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline (0.1 g), 4-aminobenzofuran (0.057 g), isopropanol (4 ml) and a solution of hydrogen chloride in isopropanol (6M, 0.06 ml) was stirred and heated to 85° C. for 3 hours. The resultant mixture was cooled to ambient temperature and the precipitate was isolated by filtration, washed in turn with a 1:1 mixture of diethyl ether and isopropanol and with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.14 g) as a dihydrochloride salt; NMR Spectrum: (DMSOd6 and CF3COOD) 2.35 (m, 2H), 2.9 (s, 3H), 3.3-4.0 (broad m, 10H), 4.05 (s, 3H), 4.35 (m, 2H), 6.9 (s, 1H), 7.4 (m, 2H), 7.45 (t, 1H), 7.65 (d, 1H), 8.05 (d, 1H), 8.3 (s, 1H), 8.8 (s, 1H); Mass Spectrum: M+H+ 448.

Workup

customthe precipitate was isolated by filtration
washwashed in turn with a 1:1 mixture of diethyl ether and isopropanol and with diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-1bf2fd4581e94495a232ce82ecfa0aeb
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939866B2

Reaction notes

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