Hydrochloric Acid → HCID 90016118, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-5-methyl-5,6-dihydro-2H-1,4-thiazin-3-amine (1.59 g, 2.25 mmol, Eq: 1.00) in dichloromethane (80 ml) at 23° C. was dropwise added TFA (12.8 g, 8.68 ml, 113 mmol, Eq: 50) and the resulting red solution was stirred at 23° C. for 3 hours, then dioxane (80 ml) was added followed by 1 M hydrochloric acid (2.25 ml, 2.25 mmol, Eq: 1.00) and stirring was continued at 23° C. for 2 hours. Poured into 25% ammonium hydroxide solution and extracted twice with dichloromethane, the combined organic layer was dried over Na2SO4, filtered off and evaporated totally. The crude material was purified by silica gel column chromatography first with ethyl acetate to remove all non-polar byproducts, then with 7 M ammonia in methanol to obtain the (R)-5-(5-amino-2-fluorophenyl)-5-methyl-5,6-dihydro-2H-1,4-thiazin-3-amine (150 mg, 627 μmol, 27.8% yield) as a light brown solid. MS (ISP): m/z=240.1 [M+H]+.

Provenance & Evidence