HCID 67429406, compound → HCID 67261828, compound

Participants

Reaction Steps

10% Palladium on carbon (30 mg, 0.028 mmol) was taken up in methanol (1 mL) under argon. A solution of the product from Step 1 (141 mg, 0.281 mmol) in methanol (3 mL) was then added. A hydrogen balloon was attached and the flask was evacuated and backfilled with hydrogen. The mixture was allowed to stir over the weekend. The reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was taken up in methanol (3 mL) and added to a flask containing 10% Palladium on carbon (30 mg, 0.028 mmol) in 1 mL methanol. A hydrogen balloon was attached and the flask was evacuated and backfilled with hydrogen and stirred for 24 hours. The reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was taken up in methanol (3 mL) and added to a flask containing 10% Palladium on carbon (30 mg, 0.028 mmol) in 1 mL methanol. A hydrogen balloon was attached and the flask was evacuated and backfilled with hydrogen and stirred for one week. The mixture was then filtered through a plug of celite and the celite was washed methanol. The filtrate was concentrated under reduced pressure to afford methyl 2,2-dimethyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylate (87 mg, 0.17 mmol, 62% yield) as a light yellow oily solid. MS ESI: [M+H]+ m/z 505.1.

Provenance & Evidence