Hydrochloric Acid → HCID 51347042, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-chloro-4-formyl-6-hydroxybenzoate (Intermediate 86) (150 mg, 0.70 mmol), 1,2-diphenylethanone (165 mg, 0.84 mmol) and urea (126 mg, 2.1 mmol) in ethanol (5 mL) was added conc. HCl (0.2 mL) and mixture was refluxed under N2 overnight. The mixture was concentrated under reduced pressure. The residue was taken up in aqueous NaOH (2 M, 5 mL) and MeOH (5 mL) and was stirred at 50° C. under N2 atmosphere for 6 hours. The resulting mixture was cooled to room temperature and acidified with aqueous HCl (2 M, 6 mL), followed by a standard aqueous/EtOAc workup and purification by prep-HPLC (0.1% TFA as additive) to give Compound 163 (75 mg, 2-step yield 26%). 1H NMR (CD3OD 400 MHz): δ 7.30-7.25 (m, 5H), 7.15-7.05 (m, 3H), 6.95-6.87 (m, 4H), 5.26 (s, 1H). MS (ESI): m/z 421.4 [M+1]+.

Provenance & Evidence