Triethylamine → rac-2-Methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1484556Notes

Reaction equation

HRID 1484556 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](/[CH:11]=[C:12](/[C:15](=O)[CH3:16])\[C:13]#[N:14])[CH:9]=2)[NH:4][N:3]=1.[NH2:18][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][C:21]#[N:22].C(N(CC)CC)C>CC(O)C>[CH3:16][C:15]1[NH:18][C:19]([C:23]([F:26])([F:25])[F:24])=[C:20]([C:21]#[N:22])[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:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 178467936HCID 178467936, compound

Product 1

HCID 178428418rac-2-Methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 5.4 g (24.0 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A) and 13.05 g (95.9 mmol) 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation: A. W. Lutz, U.S. Pat. No. 3,635,977; C. G. Krespan, J. Org. Chem. 34, 42 (1969)] in 2-propanol (27 ml) and triethylamine (0.33 ml) was stirred at reflux temperature for 15 h. After cooling, the precipitate was collected by filtration, washed twice with cold 2-propanol and dried under high vacuum to yield 5.98 g (72% of th.) of the racemic title compound as a tan solid.

Workup

  1. custompreparation
  2. temperatureat reflux temperature for 15 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration
  5. washwashed twice with cold 2-propanol
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-87ff1a497b2f47aa98331f57555398b7
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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