Formamidine acetate → 6-(4-Methoxydibenzo[b,d]furan-1-yl)-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

HRID 2383981Notes

Reaction equation

HRID 2383981 reaction equation
C[O-].[Na+].C(O)(=O)C.[CH:8]([NH2:10])=[NH:9].C[O:12][C:13]([CH:15]1[CH2:20][C:19]([C:36]#[N:37])([C:21]2[C:29]3[C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[O:26][C:25]=3[C:24]([O:34][CH3:35])=[CH:23][CH:22]=2)[CH2:18][CH2:17][C:16]1=O)=O>CO>[CH3:35][O:34][C:24]1[C:25]2[O:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[C:29]=2[C:21]([C:19]2([C:36]#[N:37])[CH2:18][CH2:17][C:16]3[N:10]=[CH:8][NH:9][C:13](=[O:12])[C:15]=3[CH2:20]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 247555955-Cyano-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexane carboxylic acid methyl ester

Product 1

HCID 1356204896-(4-Methoxydibenzo[b,d]furan-1-yl)-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of sodium methoxide (185.3 mg, 3.5 mmol) in 10 ml of methanol was added formamidine acetate (290 mg, 2.78 mmol) and the compound obtained in example 1. The reaction mass was allowed to stir at 60-70° C. for 18 hrs under nitrogen atmosphere. Most of the methanol was evaporated under vacuum and residue was purified by column chromatography to get 200 mg (67.3% yields) of the product.

Workup

  1. customMost of the methanol was evaporated under vacuum and residue
  2. customwas purified by column chromatography
  3. customto get
  4. custom200 mg (67.3% yields) of the product

Sources & evidence

ORD record
ord-bb868b052bed4346b895d9499c67da39
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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