1-Hydroxybenzotriazole → HCID 86593192, compound

HRID 2356701Notes

Reaction equation

HRID 2356701 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:15]([OH:17])=O)[CH3:2].Cl.[CH3:19][NH:20][O:21][CH3:22].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)=[N:5][C:4]=1[C:15](=[O:17])[N:20]([O:21][CH3:22])[CH3:19])[CH3:2]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43445089HCID 43445089, compound

Product 1

HCID 86593192HCID 86593192, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-ethyl-2-(4-fluorophenyl)imidazol-4-carboxylic acid (600 mg), N,O-dimethylhydroxylamine hydrochloride (325 mg), 3-ethyl-1-(3-dimethylaminopropyl)carbodiimide hydrochloride (540 mg), 1-hydroxybenzotriazole (381 mg) and triethylamine (0.54 ml) in N,N-dimethylformamide (9 ml) was stirred at room temperature overnight. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel flush column chromatography (solvent: hexane:ethyl acetate=2:1) to obtain 5-ethyl-2-(4-fluorophenyl)-4-(N-methoxy-N-methylcarbamoyl)imidazole (656 mg) as colorless powder.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by silica gel
  6. customflush column chromatography (solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6def0c5cb94c46afaa8d3db960a4c5d2
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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