Hydrazine hydrate (1:1) → 1-ethyl-4-(3-amino-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

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Reaction Steps

A mixture of 1-ethyl-4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (1 eq), from Synthetic Example 8, and hydrazine hydrate (110 eq) in n-butyl alcohol (75 mL) was kept at 80° C. for 5 hr. The mixture was cooled and concentrated. To the residue, sodium bicarbonate solution (sat.) was added and the mixture was extracted with ethyl acetate. The organic phases were combined, dried, and concentrated to afford 1-ethyl-4-(3-amino-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (Cpd. No. 294, Table 7). 1H-NMR (400 MHz, DMSO-D6): δ=11.43 (s, 1H), 7.51 (s, 1H), 7.26 (d, 1H), 7.12 (d, 1H), 5.37 (s, 2H), 4.32 (s, 1H), 3.67 (q, 2H), 2.27 (s, 6H), 1.18 (t, 3H) ppm.

Provenance & Evidence