Acetamidine monohydrochloride → 6-(4-Methoxydibenzo[b,d]furan-1-yl)-2-methyl-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

HRID 2383988

Reaction equation

CO[C:3]([CH:5]1[CH2:10][C:9]([C:26]#[N:27])([C:11]2[C:19]3[C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[O:16][C:15]=3[C:14]([O:24][CH3:25])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=O)=[O:4].Cl.[C:30]([NH2:33])(=[NH:32])[CH3:31].C[O-].[Na+]>CO>[CH3:25][O:24][C:14]1[C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[C:19]=2[C:11]([C:9]2([C:26]#[N:27])[CH2:8][CH2:7][C:6]3[N:32]=[C:30]([CH3:31])[NH:33][C:3](=[O:4])[C:5]=3[CH2:10]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of the compound obtained in example 1 (200 mg, 0.53 mol), acetamidine HCl (124.5 mg, 1.32 mmol) and sodium methoxide (98.3 mg, 1.85 mmol) in 7 ml of methanol was stirred at 60-70° C. for 18 hrs under nitrogen atmosphere. Once the reaction is complete, the reaction mass was evaporated under vacuum and the residue was diluted with ethyl acetate and water. The organic layer was washed with water followed by brine, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography to get 200 mg (40% yields) of the solid product. MP-more than 300° C.

Workup

customthe reaction mass was evaporated under vacuum
additionthe residue was diluted with ethyl acetate and water
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customThe crude product was purified by column chromatography
customto get
custom200 mg (40% yields) of the solid product
customMP-more than 300° C.

Sources & evidence

ORD record: ord-f207b6cf48e449ce8d09a58a8266a6cc
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263648B2

Linked notes

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