Triethylamine → HCID 178499094, compound

HRID 920683Notes

Reaction equation

HRID 920683 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:27]([OH:29])=[O:28])=[N:11][CH:12]=[C:13]([C:16](=[O:26])[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:31]N(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.CO>[CH3:31][O:28][C:27]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([OH:15])[C:13]([C:16](=[O:26])[NH:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)=[CH:12][N:11]=1)=[O:29]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178522996HCID 178522996, compound

Product 1

HCID 178499094HCID 178499094, compoundYield 68.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound 13 (198 mg, 0.500 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (115 mg, 0.600 mmol) and 1-hydroxybenzotriazole (81 mg, 0.600 mmol) in dimethylformamide (3 ml) was stirred at room temperature for 1.5 hours. Then, methanol (3 ml) and triethylamine (153 ul, 1.10 mmol) were added, and the mixture was heated to reflux for 1.5 hours. The reaction solution was diluted with ethyl acetate, washed with an aqueous saturated sodium bicarbonate solution, a 10% aqueous citric acid solution, and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was washed with diethyl ether to obtain 3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-hydroxy-pyridine-2-carboxylic acid methyl ester 14 (141 mg, 60%) as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. washwashed with an aqueous saturated sodium bicarbonate solution
  4. dry with materiala 10% aqueous citric acid solution, and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-fb15890a13a7482ca3421c60f0cec7d5
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

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