2-Aminopyridine → HCID 178522124, compound

HRID 1851687Notes

Reaction equation

HRID 1851687 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.Cl.[Cl:20][C:21]([F:26])([F:25])[C:22](O)=[O:23]>ClCCl.CN(C1C=CN=CC=1)C>[Cl:20][C:21]([F:26])([F:25])[C:22]([N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1)=[O:23]

Participants

6

Reactant 3

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

Product 1

HCID 178522124HCID 178522124, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-aminopyridine in an amount of 200 mg (2.13 mmol) was dissolved in 5 mL of dichloromethane, following which 491 mg (2.55 mmol) of EDC-HCl, 311 mg (2.55 mmol) of DMAP and 187 μL (2.23 mmol, 290 mg) of chlorodifluoroacetic acid were added in this order and the mixture was stirred overnight. Following reaction completion, the reaction mixture was diluted with dichloromethane, washed with water and 1% hydrochloric acid, then dried over anhydrous magnesium sulfate, giving 105 mg of 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide (yield, 24%).

Workup

  1. additionwere added in this order
  2. customreaction completion
  3. washwashed with water and 1% hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-fd6201eb58ca4fbf8693d46c4aa6a4c1
Source dataset
uspto-grants-2015_02
Patent number
US08957214B2

Reaction notes

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