(2Z)-3-Amino-2-butenenitrile → 2,6-Dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 218490

Reaction equation

HRID 218490 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=O)[CH:9]=2)[NH:4][N:3]=1.[NH2:13]/[C:14](/[CH3:18])=[CH:15]\[C:16]#[N:17]>C(O)(=O)C>[CH3:18][C:14]1[NH:13][C:9]([CH3:8])=[C:10]([C:2]#[N:3])[CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])[C:15]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 178434286HCID 178434286, compound

Product 1

HCID 1784284222,6-Dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrileYield 115.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 17.0 g (106.13 mmol) 3-methyl-1H-indazole-5-carbaldehyde, from Synthetic Preparation 10, and 17.86 g (217.57 mmol) 3-aminocrotononitrile were dissolved in 340 mL acetic acid and refluxed for 3 hours. After stirring overnight at room temperature the mixture was cooled with an ice bath, filtered and washed with a small amount of acetic acid. The product was dried under vacuum at 60° C. to afford 1,4-dihydro-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-3,5-pyridinedicarbonitrile (17.7 g, 57.6%) (Cpd. No. 81, Table 2). 1H-NMR (DMSO-D6): δ=12.68 (s, 1H), 9.51 (s, 1H), 7.53 (s, 1H), 7.49 (d, 1H), 7.27 (d, 1H), 4.50 (s, 1H), 2.49 (s, 3H), 2.05 (s, 6H) ppm. MS (ES+): 290.42 (M++1, 100%).

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturewas cooled with an ice bath
  3. filtrationfiltered
  4. washwashed with a small amount of acetic acid
  5. customThe product was dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-dff0dccf009e4ea2b7036a40b44622a6
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Linked notes

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