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Triethylamine → HCID 178499094, compound

HRID 1622919
Notes
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Reaction equation

HRID 1622919 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 69%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 6228DimethylformamideSolvent
HCID 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, 69%) 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-7e6944ec0fc04476a35f13f307f0077a
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778943B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes