Phthalamide → HCID 22172592, compound

Participants

Reaction Conditions

Reaction Steps

Alternative Preparation of Formula I where R1, R3 and R4 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H; R7 is 3-Amino-propy; R8 is —C(O)—R9 where R9 is p-Methyl-phenyl-; W, Y and Z are —C═; and X is —N═: A phthalamide-protected precursor to Formula I, N-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[4,3-d]pyrimidin-2-yl)-2-methyl-propyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]4-methyl-benzamide (300 mg, 0.488 mmol) and anhydrous hydrazine (98 mg, 3.06 mmol) in EtOH (12 mL) is refluxed for 3.0 h. The reaction is cooled to 5° C. and a precipitate is filtered off. The filtrate is concentrated in vacuo and purified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent) to provide the title compound, N-(3-amino-propyl)-N-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[4,3-d]pyrimidin-2-yl)-2-methyl-propyl]4-methyl-benzamide.

Provenance & Evidence