(2Z)-3-Amino-2-butenenitrile → 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-N-methoxy-N-methyl-1H-indazole-3-carboxamide

HRID 218485

Reaktionsgleichung

Reaktionsgleichung von HRID 218485
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])=O.[NH2:18]/[C:19](/[CH3:23])=[CH:20]\[C:21]#[N:22]>CC(O)=O.CCOC(C)=O>[C:21]([C:20]1[CH:1]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][N:7]=[C:6]3[C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[C:5]([C:6]#[N:7])=[C:4]([CH3:3])[NH:18][C:19]=1[CH3:23])#[N:22]

Komponenten

5

Edukt 2

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 249587435-formyl-N-methoxy-N-methyl-1H-indazole-3-carboxamide

Produkt 1

HCID 249616635-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-N-methoxy-N-methyl-1H-indazole-3-carboxamideAusbeute 160,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-formyl-N-methoxy-N-methyl-1H-indazole-3-carboxamide (400 mg, 1.72 mmol) from Synthetic Preparation 6, and 3-aminocrotononitrile (299 mg, 2.12 mmol) in HOAc (5 mL) was kept at 110° C. for 2 hr. After cooling to rt, the reaction mixture was diluted with EtOAc, washed with brine, dried, and concentrated. The crude product was purified by flash chromatography to afford 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-N-methoxy-N-methyl-1H-indazole-3-carboxamide (500 mg, 80.5%) (Cpd. No. 143, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=9.65 (s, 1H), 7.85 (s, 1H), 7.65 (d, 1H), 7.38 (d, 1H), 4.58 (s, 1H), 3.78 (s, 3H), 3.44 (s, 3H), 2.03 (s, 6H) ppm.

Aufarbeitung

  1. washwashed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f0cd953942ab444b89dcc5919ad5a0e3
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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