2-Aminopyridine → HCID 178522123, compound

HRID 2199263Notes

Reaction equation

HRID 2199263 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.Cl.[F:20][C:21]([F:29])([F:28])[C:22]([F:27])([F:26])[C:23](O)=[O:24]>ClCCl.CN(C1C=CN=CC=1)C>[F:26][C:22]([F:27])([C:21]([F:29])([F:28])[F:20])[C:23]([N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1)=[O:24]

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 62356Pentafluoropropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 178522123HCID 178522123, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In 15 ml of anhydrous dichloromethane, 300 mg (3.19 mmol) of 2-aminopyridine was dissolved. To this solution, 919 mg (4.78 mmol) of EDC-HCl, 583 mg (4.78 mmol) of DMAP, and 397 μl (628 mg, 3.83 mmol) of pentafluoropropionic acid were added in this order, followed by stirring at room temperature overnight. After completion of the reaction, the reaction liquid was diluted with dichloromethane, washed once with water, and twice with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Thus, 85 mg of 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide was obtained (Percentage Yield: 11%).

Workup

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

Sources & evidence

ORD record
ord-19f12aac167d49778260dac24bb32e5d
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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