3-Amino-4,4-difluorobut-2-enenitrile → HCID 178428420, compound

HRID 1484555Notes

Reaction equation

HRID 1484555 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]([CH:23]([F:25])[F:24])=[CH:20][C:21]#[N:22]>CC(O)C.C(N(CC)CC)C>[F:24][CH:23]([F:25])[C:19]1[NH:18][C:15]([CH3:16])=[C:12]([C:13]#[N:14])[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:20]=1[C:21]#[N:22]

Participants

5

Reactant 2

HCID 762236343-Amino-4,4-difluorobut-2-enenitrileHCID 178467936HCID 178467936, compound

Product 1

HCID 178428420HCID 178428420, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 3.42 g (15.2 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A) and 7.27 g (60.7 mmol) 3-amino-4,4-difluorobut-2-enenitrile [obtainable by Thorpe reaction of acetonitrile with 2,2-difluoroacetonitrile, cf. Org. React. 15, 1 (1967), ibid. 31, 1 (1984)] in 2-propanol (20 ml) and triethylamine (0.21 ml) was stirred at reflux temperature overnight. After cooling, the precipitate was collected by filtration and washed twice with cold 2-propanol. The crude product was purified by silica gel chromatography (tert-butyl methyl ether/ethanol gradient, final mixture 94:6 v/v) to yield 0.36 g (7% of th.) of the racemic title compound as a pale yellow solid.

Workup

  1. temperatureat reflux temperature overnight
  2. temperatureAfter cooling
  3. filtrationthe precipitate was collected by filtration
  4. washwashed twice with cold 2-propanol
  5. customThe crude product was purified by silica gel chromatography (tert-butyl methyl ether/ethanol gradient, final mixture 94:6 v/v)

Sources & evidence

ORD record
ord-abe7831e065640d583f825c0a7877f23
Source dataset
uspto-grants-2016_08
Patent number
US09422263B2

Reaction notes

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