3-Amino-4,4,4-trifluorobut-2-enenitrile → HCID 178434237, compound

HRID 1484568Notes

Reaction equation

HRID 1484568 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]([C:18]([F:21])([F:20])[F:19])=[CH:15][C:16]#[N:17]>C(O)(=O)C.CO.ClCCl>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[C:15]([C:16]#[N:17])=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[C:15]3[C:16]#[N:17])[CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 2

HCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 178434286HCID 178434286, compound

Product 1

HCID 178434237HCID 178434237, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 50 mg (0.31 mmol) 3-methyl-1H-indazole-5-carbaldehyde (Example 1A), 106 mg (0.78 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)] and a trace amount of powdered 4 Å molecular sieve in acetic acid (0.30 ml) was heated to reflux temperature for 2 h. After cooling, the reaction mixture was diluted with methanol/dichloromethane and filtered. The filtrate was evaporated, and the residue was purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to give 19 mg (15% of th.) of the title compound.

Workup

  1. custompreparation
  2. temperatureto reflux temperature for 2 h
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue was purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-86616a0c72114a52af826ada1351f932
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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