Pyridine → HCID 33240192, compound

HRID 1507769Notes

Reaction equation

HRID 1507769 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:38][CH:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41].N1C=CC=CC=1>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:38][CH:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[O:11])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 98372-(4-Fluorophenyl)acetic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 33240192HCID 33240192, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluorophenylacetic acid (4.5 g, 29.3 mmol) and 1-hydroxybenzotriazole (4.35 g, 32.2 mmol) in dichloromethane (140 ml) was added dicyclohexylcarbodiimide (6.65 g, 32.2 mmol). The reaction mixture was stirred at room temperature for 2 hours. The resulting solution was cooled to 00° C., and then a solution of diethyl aminomalonate hydrochloride (6.2 g, 29.3 mmol) in pyridine (4.5 ml, 29.3 mmol) and DMF (10 ml) was added. The temperature was allowed to rise to ambient temperature. After 1 hour, the reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and a 5% NaHCO3 solution. The organic layer was washed with water, brine and dried over Na2SO4. After removing the solvents, the crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 50:1) to yield the title compound as a white solid (8.5 g, 93%).

Workup

  1. temperatureThe resulting solution was cooled to 00° C
  2. customto rise to ambient temperature
  3. waitAfter 1 hour
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. customAfter removing the solvents
  9. customthe crude residue was purified by flash chromatography on silica (CH2Cl2/MeOH 50:1)

Sources & evidence

ORD record
ord-8404decad1184d0799a72d015264ce4c
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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