Isoamyl Nitrite → HCID 59161259, compound

Participants

Reaction Steps

Add (R)-N-[6-(5-Amino[1,3,4]thiadiazole-2-yl)-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]isobutyramide (Example 126) (0.104 g, 0.224 mmol) to a solution of isoamylnitrite (0.039 g, 0.337 mmol) in DMF at 60° C. and heat for 1 h. Quench reaction onto water and extract with EtOAc to give 80 mg of a yellow solid. Purify over silica eluting with 25-90% EtOAc/hexanes gradient to give 20 mg (20%). MS (ES) m/z 449 (M+1); 1H NMR (DMSO-d6): δ 9.56 (s, 1H), 8.08 (s, 1H), 7.89 (d, 1H), 7.77 (d, 1H), 7.57 (d, 1H), 7.38 (dd, 1H), 7.12 (dd, 2H), 6.84-6.94 (m, 2H), 5.44 (s, 2H), 4.05 (m, 1H), 3.07 (dd, 1H), 2.70-2.84 (m, 2H), 2.63 (m, 2H), 2.41 (septet, 1H), 2.00 (m, 1H), 1.88 (m, 1H), 1.04 (dd, 6H).

Provenance & Evidence