Isopropanol → HCID 12150234, compound

HRID 392172Notes

Reaction equation

Cl[C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]([C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=4)[N:18]=[C:17]([NH:29][CH3:30])[N:16]=3)[CH:12]=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1.Cl.[CH3:34][NH:35][CH3:36].C(N(CC)CC)C.C(O)(C)C>C(OCC)(=O)C.O1CCCC1>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[C:17]([NH:29][CH3:30])[N:16]=[C:15]2[C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:31]=[CH:32][C:2]([N:35]([CH3:36])[CH3:34])=[N:3][CH:4]=2)[CH:10]=1

Participants

Conditions

Temperature: 130 °C

Procedure

225 mg of 4-[3-(6-chloronicotinoylamino)phenyl]-6,7-dimethoxy-2-methylaminoquinazoline obtained in Example 29, 122 mg dimethylamine hydrochloride and 304 mg triethylamine were suspended in a mixed solvent of 5 ml isopropanol and 5 ml tetrahydrofuran and stirred at 130° C. for 18 hours in a sealed tube. Ethyl acetate was added thereto, and it was washed with water twice and with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (hexane:ethyl acetate=1:3). The product was recrystallized from hexane-ethyl acetate to give 185 mg of the title compound as pale yellow crystals.

Workup

washit was washed with water twice
dry with materialwith brine, and then dried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe crude product was purified
customseparated by silica gel column chromatography (hexane:ethyl acetate=1:3)
customThe product was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record: ord-e4a0478477c94bc4be15647dd7510069
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800644B2

Reaction notes

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