Diisopropylethylamine → HCID 178523063, compound

HRID 606380Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate obtained according to the methods described in Journal of Organic Chemistry (1978), 43(23), 4485-7 and the like (200 mg, 0.917 mmol), 1-(2-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}pyridin-4-yl)methanamine hydrochloride obtained in Reference Example is (343 mg, 1.19 mmol) and diisopropylethylamine (462 mg, 3.57 mmol) in DMA (5 mL) was stirred at 90° C. for 15 hr. After cooling the mixture to room temperature, the resulting solid was collected by filtration, and washed with ethanol. The obtained crude powder was recrystallized from ethanol to give the title compound as a white powder (135 mg, 35%).

Workup

customobtained
temperatureAfter cooling the mixture to room temperature
filtrationthe resulting solid was collected by filtration
washwashed with ethanol
customThe obtained crude powder
customwas recrystallized from ethanol

Sources & evidence

ORD record: ord-6a4ef7e3be68446e9e15ba8d14b4c34a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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