2-Methoxyethylamine → HCID 22063892, compound

HRID 1828203Notes

Reaction equation

HRID 1828203 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([C:20]4[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=4)=[N:14][N:15]([CH2:17][CH:18]=O)[CH:16]=3)=[CH:11][C:6]=2[N:5]([CH2:27][CH3:28])[C:4]1=[O:29])[CH3:2].[CH3:30][O:31][CH2:32][CH2:33][NH2:34]>C1C=CC=CC=1>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([C:20]4[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=4)=[N:14][N:15]([CH2:17][CH2:18][NH:34][CH2:33][CH2:32][O:31][CH3:30])[CH:16]=3)=[CH:11][C:6]=2[N:5]([CH2:27][CH3:28])[C:4]1=[O:29])[CH3:2]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 86587987HCID 86587987, compound

Product 1

HCID 22063892HCID 22063892, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a benzene (3 mL) solution of [4-(1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-m-tolyl-pyrazol-1-yl]-acetaldehyde (0.034 g) was added methoxyethylamine (0.03 mL) and 4 Å molecular sieves. The reaction was allowed to stand at 23° C. for 1 hour then was filtered and concentrated. The resulting oil was diluted with methanol (2 mL), 4 Å molecular sieves were added and the mixture was treated with sodium cyanoborohydride (0.02 g). After stirring for 18 hours the mixture was poured onto ethyl acetate/saturated sodium bicarbonate and extracted. The organic layer was dried over sodium sulfate and concentrated. Preparative thin layer chromatography gave 1,3-Diethyl-5-{1-[2-(2-methoxy-ethylamino)-ethyl]-3-m-tolyl-1H-pyrazol-4-yl}-1,3-dihydro-benzoimidazol-2-one (0.014 g). Subsequent treatment with 1M hydrochloric acid in ether gave the hydrochloride salt.

Workup

  1. filtrationthen was filtered
  2. concentrationconcentrated
  3. additionThe resulting oil was diluted with methanol (2 mL), 4 Å molecular sieves
  4. additionwere added
  5. additionthe mixture was treated with sodium cyanoborohydride (0.02 g)
  6. additionwas poured onto ethyl acetate/saturated sodium bicarbonate
  7. extractionextracted
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-de977f1a1af5421a88e3cda9152ba99f
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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