Acetonitrile → HCID 86749354, compound

Participants

Reaction Steps

To a solution of 154 mg (0.344 mmol) of 3-[trans-3-hydroxy-2,2-dimethyl-4-(1-oxo-1,3-dihydroisoindol-2-yl)-chroman-6-yl]-4-isopropoxy-cyclobut-3-ene-1,2-dione as prepared in Example 3 in CH3CN was bubbled ammonia gas for 30 min. The reaction mixture was then sealed and stirred for 16 h. The reaction mixture was concentrated. Flash chromatography (CH2Cl2 : MeOH: NH4OH (94.75/3.5/1.75)) followed by crystallization from THF and petroleum ether gave 136 mg of the title compound as a white solid, mp>250° C.: 1H-NMR (DMSO-d6 ; 400 MHz) δ8.90 (br s, 1 H), 8.76 (br s, 1 H), 7.7-7.8 (m, 3 H), 7.51-7.63 (m, 3 H), 6.98 (d, 1 H), 1.48 (s, 3 H), and 1.27 ppm (s, 3 H); IR (KBr) 1780, 1730, 1670, and 1640 cm-1 ; mass spectrum (+CI), m/e 405. Anal. Calcd. for C23H20N2OS: C, 68.31; H, 4.98; N, 6.93 Found.: C, 67.91; H, 5.12; N, 6.78.

Provenance & Evidence