3-Amino-4,4,4-trifluorobut-2-enenitrile → HCID 178437993, compound

HRID 1484565Notes

Reaction equation

HRID 1484565 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[CH:12]=[C:13](/[C:16](=O)[CH3:17])\[C:14]#[N:15])[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[NH2:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][C:22]#[N:23]>C(O)C.CC(O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]3[C:21]([C:22]#[N:23])=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:16]([CH3:17])=[C:13]3[C:14]#[N:15])[CH:10]=2)[NH:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 178437998HCID 178437998, compound

Product 1

HCID 178437993HCID 178437993, compound

Reagents, catalysts & solvents 1

HCID 22179027Isopropanol ethanolSolvent

Procedure

A suspension of 300 mg (1.25 mmol) (2E)-2-[(3-ethyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 11A) and 853 mg (6.27 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 ethanol/2-propanol (8:1 v/v, 1.0 ml) was stirred at reflux temperature for 24 h. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to yield 59 mg (13% of th.) of the racemic title compound.

Workup

  1. custompreparation
  2. temperatureat reflux temperature for 24 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-d2fff68459dc4e7f9df7a633338f3947
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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