Hydrazine hydrate (1:1) → 4-(3-amino-1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 218477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218477
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]2[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]2[C:20]#[N:21])[CH:6]=[CH:7][C:8]=1F)#[N:2].O.[NH2:23][NH2:24]>C(O)CCC>[NH2:2][C:1]1[C:3]2[C:8](=[CH:7][CH:6]=[C:5]([CH:10]3[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]3[C:20]#[N:21])[CH:4]=2)[NH:24][N:23]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 597632464-(3-Cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

Produkt 1

HCID 249594654-(3-amino-1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrileAusbeute 57,01 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (9.5 g, 34.14 mmol), from Synthetic Example 1, and hydrazine hydrate (10 g, 312 mmol) in n-butyl alcohol (75 mL) was kept at 80° C. for 5 hr. The mixture was cooled and concentrated. Sodium bicarbonate solution (sat.) was added to the residue, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried, and concentrated to afford 4-(3-amino-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (5.6 g, 57.01%) as a pale yellow solid (Cpd. No. 82, Table 2). 1H-NMR (300 MHZ, DMSO-D6): δ=11.39 (br. s, 1H), 9.47 (br. s, 1H), 7.50 (m, 1H), 7.20 (d, 1H), 7.11 (dd, 1H), 5.34 (br. s, 2H), 4.34 (s, 1H), 2.01 (s, 6H) ppm.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e02bb167ecf24f06ba7237fe2a701dd2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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