Difluoroacetic acid → HCID 178522122, compound

HRID 2199264Notes

Reaction equation

HRID 2199264 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][CH:9]([F:13])[C:10](O)=[O:11].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C>[F:8][CH:9]([F:13])[C:10]([N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1)=[O:11]

Participants

6

Reactant 3

HCID 9788Difluoroacetic acidHCID 104392-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 178522122HCID 178522122, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In 10 ml of anhydrous dichloromethane, 400 mg (4.26 mmol) of 2-aminopyridine was dissolved. To this solution, 322 μl (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCl, and 622 mg (5.11 mmol) of DMAP were added, followed by stirring at room temperature for 61 hours. After completion of the reaction, the reaction liquid was diluted with dichloromethane, and washed once with water, and twice with 1% HCl aq., then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Thus, 102 mg of 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide was obtained (Percentage Yield: 14%).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. washwashed once with water
  4. dry with materialtwice with 1% HCl aq., then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4866e59dc8234aacba5460889adfed29
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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