1,1'-Carbonyldiimidazole → (1S,2R)-4'-(4-chlorophenyl)-2,2',3'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-9'(8'H)-one

Participants

Reaction Conditions

Reaction Steps

A disposable tube was charged with (1S,2R)-5′-(4-chlorophenyl)-2′-hydrazono-2,6′,7′-trimethyl-1′,2′-dihydrospiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepine] (24 mg, 0.067 mmol) and a stir bar. THF (1.5 mL, 0.05 M) was added, followed by CDI (13.01 mg, 0.080 mmol), and the solution was stirred 85° C. 4 h. At 4 h, more CDI (26 mg, 0.160 mmol) was added, and the reaction was stirred at 85° C. The reaction was concentrated and purified by reverse phase chromatography (water/acetonitrile with 0.1% TFA) to give (1S,2R)-4′-(4-chlorophenyl)-2,2′,3′-trimethylspiro[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-9′(8′H)-one (2,2,2-trifluoroacetic acid salt) (Compound 222) as a yellow amorphous solid (17 mg). LRMS (M+H)+: 385 m/z. 1H NMR (400 MHz, DMSO-d6) δ 12.08 (s, 1H), 7.49 (d, J=8.90 Hz, 2H), 7.42 (d, J=8.70 Hz, 2H), 2.34 (s, 3H), 1.52 (s, 3H), 1.18 (s, OH), 1.16 (s, 1H), 1.15 (s, 1H), 0.87 (br. s., 2H).

Provenance & Evidence