Potassium tert-butoxide → 1-({(5S,7S)-3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

1-{[(3S,5S)-5-methyl-1-oxaspiro[2.5]oct-5-yl]methyl}-1H-benzimidazole-6-carbonitrile (150 mg, 0.533 mmol), 1,1-dimethylethyl [5-(1,1-dimethylethyl)-3-isoxazolyl]carbamate (320 mg, 1.333 mmol) and potassium tert-butoxide (78 mg, 0.693 mmol) were added to a 10 mL microwave vial while nitrogen purging. Then, NMP (3 mL) was added and the vial was capped and heated to 125° C. for 16 h. The reaction was filtered and purified to give 42 mg (13.3%) of 1-({(5S,7S)-3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]dec-7-yl}methyl)-1H-benzimidazole-6-carbonitrile. 1H NMR (400 MHz, MeOH-d4) δ 8.43 (br. s., 1H), 8.19 (s, 1H), 7.82 (d, J=8.28 Hz, 1H), 7.58 (d, J=8.28 Hz, 1H), 6.56 (s, 1H), 4.19 (s, 2H), 3.66-3.79 (m, 2H), 2.04 (d, J=5.77 Hz, 1H), 1.95 (d, J=14.05 Hz, 1H), 1.78-1.90 (m, 1H), 1.65-1.78 (m, 2H), 1.40-1.63 (m, 3H), 1.32 (s, 9H), 1.18 (s, 3H). MS (m/z) 448.3 (M+H+).

Provenance & Evidence