Ethanol → HCID 178522989, compound

HRID 606378Notes

Reaction equation

[NH:1]1[CH:5]=[N:4][C:3]([S:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][NH2:17])[CH:13]=[CH:14][CH:15]=2)=[N:2]1.[F:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[C:24]([C:29](OCC)=[O:30])[NH:23][C:22]2=[O:34].C(N(C(C)C)CC)(C)C.C(O)C>C1COCC1>[F:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[C:24]([C:29]([NH:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][S:6][C:3]3[N:4]=[CH:5][NH:1][N:2]=3)[CH:11]=1)=[O:30])[NH:23][C:22]2=[O:34]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 1-(3-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}phenyl)methanamine obtained in Reference Example 3 (318 mg, 1.27 mmol), ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate obtained in Reference Example 52 (100 mg, 0.423 mmol) and diisopropylethylamine (0.442 mL, 2.54 mmol) in THF (9 mL)-ethanol (3 mL) was stirred at 90° C. for 2 days. The reaction solvent was evaporated under reduced pressure, and the residue was extracted with 0.1N hydrochloric acid and THF-ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was crystallized from toluene-ethanol, and the obtained crude crystals were recrystallized from THF-IPE to give the title compound as a white powder (45.7 mg, 25%).

Workup

customThe reaction solvent was evaporated under reduced pressure
extractionthe residue was extracted with 0.1N hydrochloric acid and THF-ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was crystallized from toluene-ethanol
customthe obtained crude crystals
customwere recrystallized from THF-IPE

Sources & evidence

ORD record: ord-a4164b85123f4641bbe9f84ec65aebd5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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