Ethyl propiolate → HCID 20812144, compound

HRID 1988709Notes

Reaction equation

HRID 1988709 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]=[N+:13]=[N-:14])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[F:28])[CH3:2].[C:29]([O:33][CH2:34][CH3:35])(=[O:32])[C:30]#[CH:31]>C(O)C>[CH2:34]([O:33][C:29]([C:30]1[N:14]=[N:13][N:12]([C:10]2[CH:9]=[CH:8][C:7]3[N:3]([CH2:1][CH3:2])[C:4]([CH2:15][N:16]4[CH:20]=[CH:19][N:18]=[C:17]4[C:21]4[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=4[F:28])=[N:5][C:6]=3[CH:11]=2)[CH:31]=1)=[O:32])[CH3:35]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 22380013HCID 22380013, compound

Product 1

HCID 20812144HCID 20812144, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of crude 1-ethyl-2-{[2-(2,5-difluorophenyl)-1H-imidazol-1-yl]methyl}-5-azido-1H-benzimidazole (143 mg) and ethyl propiolate (1 eq.) in ethanol (10 mL) is heated at reflux for 6 h. The mixture is cooled, concentrated, and the residue purified by preparative silica gel chromatography to give 1-{2-[2-(2,5-Difluoro-phenyl)-imidazol-1-ylmethyl]-1-ethyl-1H-benzoimidazol-5-yl}-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester. 1H NMR (CDCl3): δ 8.51 s, (1H), 8.05 (s, 1H), 7.74 (m, 1H), 7.50-7.39 (m, 4H), 7.21-7.17 (m, 2H), 7.06 (s, 1H), 5.54 (s, 2H), 4.47 (q, 2H), 3.86 (q, 2H), 1.43 (t, 3H), 1.04 (t, 3H), LCMS MH+ 460.6.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 h
  3. temperatureThe mixture is cooled
  4. concentrationconcentrated
  5. customthe residue purified by preparative silica gel chromatography

Sources & evidence

ORD record
ord-967670ab290442bf9cf52e5181c11137
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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