Cyclohexyl isocyanate → HCID 10283168, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, a suspension of 50 mg of 5-methyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide (Example 3), 10 mg of DMAP and 25 μl of cyclohexylisocyanate in 4 ml of chloroform and 3 ml of DMF was stirred for 72 h at 70° C. The mixture was diluted with 50 ml of ethyl acetate and washed with 50 ml of 10% aqueous citric acid and 2×25 mlf of water. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel eluting with a gradient of hexane:ethyl acetate 1:1 to ethyl acetate, then with DCM containing 4% of methanol to give 38 mg of cyclohexylcarbamic acid 4-[6-(5-methylpyridine-2-sulfonylamino)-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yloxy]-but-2-ynyl ester as a beige foam. LC-MS: tR=4.89 min, [M+1]+=659.33, [M−1]−=657.25.

Provenance & Evidence