Potassium Hydroxide → 3-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(5-methyl-furan-2-yl)aniline

HRID 64104Notes

Reaction equation

HRID 64104 reaction equation
[OH-].[K+].[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:33]=[CH:32][C:12]3[N:13]([C:16]4[CH:17]=[C:18]([NH:28]C(=O)C)[CH:19]=[C:20]([C:22]5[O:23][C:24]([CH3:27])=[CH:25][CH:26]=5)[CH:21]=4)[CH:14]=[N:15][C:11]=3[CH:10]=2)[CH:6]=[N:5]1>C(O)C.O.C(OCC)(=O)C>[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:33]=[CH:32][C:12]3[N:13]([C:16]4[CH:17]=[C:18]([CH:19]=[C:20]([C:22]5[O:23][C:24]([CH3:27])=[CH:25][CH:26]=5)[CH:21]=4)[NH2:28])[CH:14]=[N:15][C:11]=3[CH:10]=2)[CH:6]=[N:5]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 89501159HCID 89501159, compound

Product 1

HCID 895012033-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(5-methyl-furan-2-yl)anilineYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of KOH (0.614 g, 10.94 mmol) and the compound of Example 73 (3.0 g, 7.29 mmol) in ethanol (5 ml) and water (2 ml) was heated at 60° C. for 2 h. The mixture was diluted with ethyl acetate (100 ml) and was washed with water (50 ml) and brine (25 ml). The organic phase was dried over sodium sulfate and concentrated under vacuum and the residue was purified by column chromatography to afford the product in 92% yield (2.5 g).

Workup

  1. washwas washed with water (50 ml) and brine (25 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customthe residue was purified by column chromatography
  5. customto afford the product in 92% yield (2.5 g)

Sources & evidence

ORD record
ord-0469c15a9edb4b3088fed8d9ae32ba09
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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