Acetic Acid → HCID 86695099, compound

Participants

Reaction Steps

For the preparation of the starting material compound 35.1, please see Example 35. A solution of 2-[(3R)-12-[(4-[[tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetic acid (150 mg, 0.32 mmol, 1.00 equiv), HATU (183 mg, 0.48 mmol, 1.48 equiv), DIPEA (165 mg) and 2-amino-N-methylacetamide hydrochloride (intermediate 83.5, 120 mg, 0.96 mmol, 3.0 equiv) in 10 mL of anhydrous DMF was stirred for 24 h at room temperature under nitrogen. After completion of the reaction, the resulting solution was diluted with water and extracted with 3×40 mL of ethyl acetate. The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (30:1) to afford tert-butyl N-methyl-N-(4-[[(3R)-3-([[(methylcarbamoyl)methyl]carbamoyl]methyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (130 mg, 75%) as a yellow oil. MS: m/z 532 [M+H]+.

Provenance & Evidence