HCID 73063680, compound → 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide

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Reaction Steps

A mixture of 2-(6,8-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-benzyloxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide (300 mg) in ethyl acetate (20 mL) was treated with 600 mg of 10% Pd/C (50% water) and hydrogenated at 45 psi overnight. The mixture was filtered through celite, washed with ethylacetate. The combined filtrate was concentrated to dryness, added ethanol (10 mL), ethyl acetate (10 mL) and chloroform (5 mL) and treated with 1.4 g of 10% Pd/C (50% water) and hydrogenated at 50 psi overnight. The mixture was filtered through celite, washed with a mixture of methanol and chloroform. The filtrate was concentrated to give a light yellow oil. The oil was triturated with a 5:1 of hexane:chloroform to give 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide as an off-white solid, LC-MS RT=1.8 min, M+1=439.0.

Provenance & Evidence