1,4-Dioxane → (4-Benzyloxyphenyl)-(6-iodo-7-fluoroquinazolin-4-yl)-amine hydrochloride

HRID 6827Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([I:13])[CH:11]=2)[N:6]=[CH:5][N:4]=1.O1CCOCC1.Cl.[CH2:22]([O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[ClH:2].[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]([NH:34][C:3]2[C:12]3[C:7](=[CH:8][C:9]([F:14])=[C:10]([I:13])[CH:11]=3)[N:6]=[CH:5][N:4]=2)=[CH:35][CH:36]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Prepared according to Procedure A from 4-chloro-6-iodo-7-fluoro-quinazoline hydrochloride (4.02 grams, 11.65 mmoles), anhydrous dioxane (70 ml), dichloromethane (20 ml) and 4-benzyloxyaniline hydrochloride (2.83 grams, 12 mmoles). The mixture was stirred and heated to 110° C. (oil bath temperature) for 16 hours. The mixture was cooled to room temperature and filtered to remove the precipitated solids. The solids were washed with cold anhydrous dioxane (100 ml) followed by cold anhydrous diethyl ether. The yellowish solid was collected and dried under vacuum at room temperature to yield 4.68 grams (79%) of the title compound. δH (400 MHz, DMSO-d6): 11.2(s, 1H), 9.3(d, 1H), 8.79(s, 1H), 7.64(d, 1H), 7.58(d, 2H), 7.44(d, 2H), 7.38(m, 2H), 7.31(m, 1H), 7.09(d, 2H), 5.14(s, 2H) ESI-MS m/z 472(M+1).

Workup

customPrepared
temperatureThe mixture was cooled to room temperature
filtrationfiltered
customto remove the precipitated solids
washThe solids were washed with cold anhydrous dioxane (100 ml)
customThe yellowish solid was collected
customdried under vacuum at room temperature

Sources & evidence

ORD record: ord-ce0a4ccfcaef4b198680731b618331df
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084147B2

Reaction notes

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