Sodium Hydroxide → HCID 50991219, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-furan-2-yl-isoxazole-3-carboxylic acid (CAS 98434-06-1) (77.3 mg, 0.42 mmol) in methanol (2 ml) was cooled to 0° C. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMTMM) (135 mg, 0.46 mmol) was added and the mixture stirred at 0° C. for 10 minutes. Thereafter, a solution of (RS)-5-(5-amino-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine (85 mg, 0.38 mmol) in methanol (1 ml) was added and the reaction mixture stirred at 0° C. for 2 hours, then kept at 4° C. for 16 hours. For the workup, the reaction mixture was treated at 0° C. with sodium hydroxide (1 N, 6 ml). The yellow suspension was extracted with ethyl acetate (15 ml), then the aqueous layer re-extracted with ethyl acetate (10 ml). The combined organic layers were dried over sodium sulfate and evaporated at reduced pressure. After chromatography on a Silicycle-Si-amine phase using a gradient of dichloromethane and methanol=100/0 to 90/10 the 5-furan-2-yl-isoxazole-3-carboxylic acid [3-((RS)-5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide was obtained as a white sold (16 mg, 11% of theory). Mass (calculated) C19H17FN4O4 [384.365]; (found) [M+H]+=385.

Provenance & Evidence