2-Aminopyridine → HCID 178522123, compound

HRID 1519017Notes

Reaction equation

HRID 1519017 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

2-aminopyridine (300 mg, 3.19 mmol) was dissolved in 15 mL of anhydrous dichloromethane, following which 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 and the mixture was stirred overnight at room temperature. Following reaction completion, the reaction mixture 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, affording 85 mg of 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide (yield, 11%).

Workup

  1. additionwere added in this order
  2. customreaction completion
  3. washwashed once with water and twice with 1% hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c94fe240d50a48069a77bbe56bf4c406
Source dataset
uspto-grants-2015_07
Patent number
US09073866B2

Reaction notes

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