Hydrazine → HCID 58459803, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,2S)-2-Thiophen-2-yl-cyclopropanecarboxylic acid {(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-[2-methyl-4-((S)-2-methyl-butoxy)-phenyl]-ethyl}-amide (50 mg, 0.097 mmol) dissolved in 5 mL EtOH was added anhydrous hydrazine (31 mg, 0.97 mmol), and heated to 55° C. for 1 hr with stirring. The reaction mixture was concentrated on the rotavap, and the residue redissolved in EtOAc, and washed with aq. NaHCO3, brine and dried over MgSO4. It was concentrated and purified on the neutral PREP HPLC to obtain 19 mg (51%) of the product. 1H NMR (400 MHz, MeOD) δ ppm 8.73-8.68 (d, J=5.2 Hz, 1H), 7.23-7.31 (m, 1H), 7.16 (dd, J=5.1, 1.3 Hz, 1H), 6.89 (dd, J=5.2, 3.4 Hz, 1H), 6.82 (dd, J=4.7, 2.1 Hz, 3H), 5.36-5.48 (m, 1H), 3.68-3.89 (m, 2H), 3.33-3.29 (m, 2H), 2.51-2.60 (m, 1H), 2.40 (s, 3H), 1.98 (d, J=3.7 Hz, 1H), 1.77-1.87 (m, 1H), 1.54-1.66 (m, 2H), 1.23-1.33 (m, 2H), 1.02 (d, 3H), 0.97 (d, J=6.8 Hz, 3H); m/e LCMS calcd 387.3 [(M+1)+, for C22H31N2O2S 387.3].

Provenance & Evidence