2-Aminopyridine → HCID 178522124, compound

HRID 2199260Notes

Reaction equation

HRID 2199260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.Cl.CN(C1C=CC=CN=1)C.[Cl:29][C:30]([F:35])([F:34])[C:31](O)=[O:32]>ClCCl>[Cl:29][C:30]([F:35])([F:34])[C:31]([N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1)=[O:32]

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 218852-DimethylaminopyridineHCID 66154Chlorodifluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 178522124HCID 178522124, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 5 ml of dichloromethane, 200 mg (2.13 mmol) of 2-aminopyridine was dissolved. To this solution, 491 mg (2.55 mmol) of EDC-HCl, 311 mg (2.55 mmol) of dimethylaminopyridine, and 187 μl (2.23 mmol, 290 mg) of chlorodifluoroacetic acid were added in this order, followed by stirring overnight. After completion of the reaction, the reaction liquid was diluted with dichloromethane, washed with water and with 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate. Thus, 105 mg of 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide was obtained (Percentage Yield: 24%).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. washwashed with water and with 1% hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-c36d88cb5812441cb40fd4411b1a132d
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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