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

HRID 218484Notes

Reaction equation

HRID 218484 reaction equation
[CH2:1]([N:3]1[C:8]([CH3:9])=[C:7]([C:10]#[N:11])[CH:6]([C:12]2[CH:17]=[CH:16][C:15](F)=[C:14]([C:19]#[N:20])[CH:13]=2)[C:5]([C:21]#[N:22])=[C:4]1[CH3:23])[CH3:2].O.[NH2:25][NH2:26]>C(O)CCC>[CH2:1]([N:3]1[C:8]([CH3:9])=[C:7]([C:10]#[N:11])[CH:6]([C:12]2[CH:13]=[C:14]3[C:15](=[CH:16][CH:17]=2)[NH:26][N:25]=[C:19]3[NH2:20])[C:5]([C:21]#[N:22])=[C:4]1[CH3:23])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 690425561-Ethyl-4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

Product 1

HCID 532331021-ethyl-4-(3-amino-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. additionTo the residue, sodium bicarbonate solution (sat.) was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9ccc5f5bb4bd457c82a48dee6119bfcb
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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