2-Chloro-4-hydrazinylbenzonitrile hydrochloride → 2-(3-chloro-4-cyanophenyl)-3-cyclobutyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid

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The title compound was prepared according to Method B and Method C from methyl 6-(cyclobutylmethylene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate; Preparation 19 and 2-chloro-4-hydrazinylbenzonitrile hydrochloride (Preparation 1) to give 2-(3-chloro-4-cyanophenyl)-3-cyclobutyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid (150 mg, 0.36 mmol, 65% yield) as a yellow solid. The title compound was largely present as (±)-(3RS,3aSR)-2-(3-chloro-4-cyanophenyl)-3-cyclobutyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56-1.77 (m, 4H), 1.77-1.98 (m, 3H), 2.07-2.18 (m, 1H), 2.51-2.59 (m, 1H), 2.80-2.93 (m, 1H), 2.97-3.07 (m, 1H), 3.44-3.56 (m, 1H), 4.88 (dd, J=9.40, 6.98 Hz, 1H), 7.22 (dd, J=8.86, 1.88 Hz, 1H), 7.42 (d, J=2.15 Hz, 1H), 7.67 (d, J=8.86 Hz, 1H), 7.75-7.83 (m, 2H), 8.01 (d, J=8.06 Hz, 1H). ES-MS m/z 420 (M+H)

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