Sodium Hydroxide → 3-(5-(1-Ethyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(1H-pyrrol-1-yl)aniline

HRID 64145Notes

Reaction equation

HRID 64145 reaction equation
[OH-].[Na+].[CH2:3]([N:5]1[CH:9]=[C:8]([C:10]2[CH:33]=[CH:32][C:13]3[N:14]([C:17]4[CH:18]=[C:19]([NH:28]C(=O)C)[CH:20]=[C:21]([N:23]5[CH:27]=[CH:26][CH:25]=[CH:24]5)[CH:22]=4)[CH:15]=[N:16][C:12]=3[CH:11]=2)[CH:7]=[N:6]1)[CH3:4]>C(O)C.C(OCC)(=O)C>[CH2:3]([N:5]1[CH:9]=[C:8]([C:10]2[CH:33]=[CH:32][C:13]3[N:14]([C:17]4[CH:18]=[C:19]([CH:20]=[C:21]([N:23]5[CH:27]=[CH:26][CH:25]=[CH:24]5)[CH:22]=4)[NH2:28])[CH:15]=[N:16][C:12]=3[CH:11]=2)[CH:7]=[N:6]1)[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117777681HCID 117777681, compound

Product 1

HCID 1177774783-(5-(1-Ethyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(1H-pyrrol-1-yl)anilineYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20% NaOH (5 ml) and the compound of Example 171 (0.9 g, 2.12 mmol) in 25 ml of ethanol was heated at 90° C. for 2 h. The mixture was diluted with ethyl acetate (100 ml) and the organic layer was washed with water (50 ml) and brine (25 ml). The solvent was distilled off and the residue was purified by column chromatography over silica gel to afford the compound in 78% yield (0.7 g).

Workup

  1. washthe organic layer was washed with water (50 ml) and brine (25 ml)
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by column chromatography over silica gel
  4. customto afford the compound in 78% yield (0.7 g)

Sources & evidence

ORD record
ord-73ee1750099d4b60a99f88a8ef68c5a3
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

Loading…