Thionyl Chloride → HCID 69629609, compound

Participants

Reaction Steps

To a stirred mixture of ((5S)-2-methyl-5-phenyl-1,3-oxazolin-4-yl)methan-1-ol (1.0 mg, 5.23 mmol) in methylene chloride (15 mL) was added thionyl chloride (570 μL, 7.81 mmol) dropwise at 0° C. The resulting mixture was stirred under an atmosphere of nitrogen for 8 hours, then concentrated under a reduced pressure to afford (5S)-4-chloromethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole as a white solid (960 mg, M+1=210.1). B. To a stirred mixture of (2R)-3-((2S)-2-methylpiperazinyl)-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol (51 mg, 0.13 mmol) in tert-amylalcohol (5 mL) was added triethylamine (90 μL, 0.65 mmol), followed by (5S)-4-chloromethyl-2-methyl-5-phenyl-1,3-oxazole (29 mg, 0.14 mmol). The resulting mixture was stirred at 95° C. for 12 hours, concentrated, and purified by preparative chromatograph (1:19 MeOH:CH2Cl2) to afford (2R)-3-{(2S)-4-[((4S,5S)-2-methyl-5-phenyl(1,3-oxazolin-4-yl))methyl]-2-methylpiperazinyl}-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol; (5 mg, M+1=495.2). B. Preparation of a Compound of Formula I

Provenance & Evidence