Ammonia → 6'-Bromo-4,4-difluoro-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine

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Reaction Conditions

Reaction Steps

6′-Bromo-4,4-difluoro-5″-methyl-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazole]-4″(3″H)-thione (Example 27 Step 3, 57 mg, 0.14 mmol) in ammonia (7 M in MeOH) (1.5 mL, 10.5 mmol) was heated in a microwave reactor for 40 min at 100° C. The mixture was concentrated, re-dissolved in ammonia (7 M in MeOH) (1.5 mL, 10.5 mmol) and heated with MW for 40 min at 100° C. The mixture was concentrated. Purification of the crude product by flash chromatography using a gradient of CHCl3/MeOH 40:1-30:1-20:1 gave the title compound (21 mg, 39% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 1.15-1.29 (m, 1 H), 1.47 (m, 2 H), 1.61-1.73 (m, 1 H), 1.73-1.97 (m, 4 H), 2.18 (s, 3 H), 2.98 (d, 1 H), 3.08 (d, 1H), 6.67 (m, 3 H), 7.26 (d, 1 H), 7.37 (dd, 1 H); MS (ES+) m/z 382 [M+H]+.

Provenance & Evidence