Isopropanol → HCID 12150234, compound

HRID 275737Notes

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-999dd6498ae743b99d3eb165b99a9794
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352989B1

Reaction notes

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