Dichloromethane → HCID 86653737, compound

HRID 2088864Notes

Reaction equation

HRID 2088864 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.Cl[C:14]1[C:19]([CH2:20][C:21]([OH:23])=O)=[CH:18][CH:17]=[CH:16][N:15]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.[Cl:31]CCl>C1COCC1>[Cl:31][C:16]1[N:15]=[CH:14][C:19]([CH2:20][C:21]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 104392-AminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 147395442-(2-Chloropyridin-3-yl)acetic acid

Product 1

HCID 86653737HCID 86653737, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an inert atmosphere, 6.23 g (38.5 mmol) of N,N-carbonyldiimidazole are 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, 5.43 g (57.7 mmol) of 2-aminopyridine are then added and the mixture is refluxed for 2 hours. 200 ml of dichloromethane are added to the reaction mixture, cooled to room temperature, and the organic phase thus obtained is washed with saturated ammonium chloride solution and then with aqueous sodium hydroxide solution (1N), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate, from 0% to 70% ethyl acetate). 5.6 g of compound are obtained in the form of a white powder. Yield 65%. Melting point: 130° C. MH+: 248.1 (tr: 5.45 min., condition 1).

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customthe organic phase thus obtained
  3. washis washed with saturated ammonium chloride solution
  4. dry with materialwith aqueous sodium hydroxide solution (1N), dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate, from 0% to 70% ethyl acetate)

Sources & evidence

ORD record
ord-5b6acb6ef8234e9dad3279e9355dbaba
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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