HCID 178490078, compound → HCID 178490077, compound

HRID 1012160Notes

Reaction equation

HRID 1012160 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:15]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:19]=2[O:28][CH3:29])=[CH:14][NH:13][N:12]=1)=O>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:11]1[C:15]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[C:22]([C:24]([CH3:25])([CH3:26])[CH3:27])[CH:21]=[CH:20][C:19]=2[O:28][CH3:29])=[CH:14][NH:13][N:12]=1

Participants

3

Reactant 1

HCID 178490078HCID 178490078, compound

Product 1

HCID 178490077HCID 178490077, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

4-(5-tert-Butyl-2-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid (2-amino-phenyl)-amide (848 mg, 2.08 mmol) was dissolved in acetic acid (150 ml) and refluxed at 140° C. for 3 hours. The solution was left to cool, the solvent removed in vacuo and the resulting solid dried through azeotrope with methanol and toluene. The crude product was purified by column chromatography [SiO2, EtOAc/petrol (2:1)] to give N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-5-tert-butyl-2-methoxy-benzamide (500 mg, 62% yield) as a pale yellow powder. (LC/MS: Rt 3.44, [M+H]+ 390, acidic method.

Workup

  1. waitThe solution was left
  2. temperatureto cool
  3. customthe solvent removed in vacuo
  4. dry with materialthe resulting solid dried through azeotrope with methanol and toluene
  5. customThe crude product was purified by column chromatography [SiO2, EtOAc/petrol (2:1)]

Sources & evidence

ORD record
ord-cacd34c9fd7d48f99e33c4e0bb2029b1
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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