Sulfuric Acid → HCID 67994751, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of methyl 4-cyano-1-(3-(8-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-5H-pyrido[4,3-b]indole-7-carboxylate (0.172 g, 0.342 mmol) and 90% aqueous Sulfuric acid (2.000 ml, 36.8 mmol) was heated at 60° C. for 15-30 minutes. LC-MS showed complete conversion to the desired product plus the corresponding carboxylic acid as a minor product. The reaction mixture was cooled to 0° C. and carefully neutralized to approx. pH=5-6 with 50% NaOH solution then stirred overnight. The reaction mixture was filtered and the residue dried under vacuum overnight to give methyl-4-carbamoyl-1-(3-(8-fluoro-4-oxoquinazolin-3(4H)-yl)-2-methylphenyl)-5H-pyrido[4,3-b]indole-7-carboxylate as a tan solid. [0.143 g, 0.274 mmol, 80% yield] The product had an HPLC Retention Time=2.798 minutes[mixture of isomers] [4 min grad, 10% MeOH/water to 90% MeOH/water, 0.1% TFA, YMC COMBISCREEN® ODS-A, 4.6×50 mm, 220 nM]; LC/MS+1 522.4.

Provenance & Evidence