Ethyl 3-methoxybenzimidate → HCID 59511775, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude (S)-(+)-2-amino-5-(3-hydroxy-2-methylpropoxy)-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE VII.1) (223 mg, 0.70 mmol) (prepared in Procedure VIII) and ethyl 3-methoxybenzimidate*HCl (INTERMEDIATE III.2) (449 mg, 2.08 mmol) in anhydrous ethanol (5 mL) was heated to 80° C. in a tightly capped scintillation vial for 16 h. This was then cooled and concentrated in vacuo. The crude residue was partitioned between dichloromethane/2-propanol (3:1, v/v) and water and the aqueous extracted with further dichloromethane/2-propanol (3:1, v/v). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The crude solid thus obtained was suspended in cold ethyl acetate and collected by filtration affording (S)-(+)-2-[6-(3-hydroxy-2-methylpropoxy)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (145 mg, 0.33 mmol, 43% from 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]benzoic acid) as a light brown solid.

Provenance & Evidence