Dichloromethane → HCID 86653737, compound

HRID 467839Notes

Reaction equation

HRID 467839 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([OH:11])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[Cl:19]CCl>C1COCC1>[Cl:19][C:4]1[N:3]=[CH:2][C:7]([CH2:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 104392-AminopyridineHCID 147395442-(2-Chloropyridin-3-yl)acetic acid

Product 1

HCID 86653737HCID 86653737, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under inert atmosphere, 6.2 g (38.5 mmol) of N,N-carbodiimidazole is added to a suspension of 6 g (35 mmol) of 2-chloropyridylacetic acid in anhydrous THF (90 ml) at room temperature. The reaction mixture is stirred at this temperature for 2 hours, then 5.4 g (57.7 mmol) of 2-aminopyridine is added and the mixture is heated for 2 hours under reflux. 200 ml of dichloromethane is added to the reaction mixture, cooled beforehand to room temperature, the organic phase thus obtained is washed with a saturated solution of ammonium chloride, then with an aqueous solution of soda (1N), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography (eluent: A/B=dichloromethane/ethyl acetate 0% to 70% of B). 5.6 g of compound is obtained in the form of a white powder. Yield 65%. Melting point: 130° C. MH+: 248 (Tr: 5.6 min, condition 1).

Workup

  1. temperaturethe mixture is heated for 2 hours
  2. temperatureunder reflux
  3. customthe organic phase thus obtained
  4. washis washed with a saturated solution of ammonium chloride
  5. dry with materialwith an aqueous solution of soda (1N), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel flash chromatography (eluent

Sources & evidence

ORD record
ord-923707c4f06d4f7893fb8f008a288524
Source dataset
uspto-grants-2014_01
Patent number
US08623893B2

Reaction notes

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