1-Hydrazinoisoquinoline → 1-(isoquinolin-1-yl)-N3-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)-1H-1,2,4-triazole-3,5-diamine

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Reaction Steps

A solution of (Z)-phenyl N′-cyano-N-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)carbamimidate (36 mg, 0.1 mmol) and 1-hydrazinoisoquinoline in N-methyl-2-pyrrolidone (0.5 mL) was shaken at 100° C. for 3 hours. After cooling to ambient temperature, the volatiles were evaporated under reduced pressure. The residue was purified by HPLC eluting with acetonitrile-water to provide 1-(isoquinolin-1-yl)-N3-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)-1H-1,2,4-triazole-3,5-diamine, compound #1; 1H NMR (CD3OD, 300 MHz) 8.98 (d, J=8.4 Hz, 1H), 8.36 (d, J=5.7 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H), 7.84-7.58 (m, 4H), 7.26 (dd, J=2.4, 8.7 Hz, 1H), 6.99 (d, J=9.0 Hz, 1H), 5.05 (s, 2H), 3.76 (m, 2H), 3.65 (m, 2H), 3.30 (m, 3H), 2.11 (m, 4H) ppm; MS (ES) 427.16 (M+H).

Provenance & Evidence