Benzoyl chloride → Phenyl-n-(3-phenyl(1h-indazol-5-yl))carboxamide

HRID 1353658Notes

Reaction equation

HRID 1353658 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.C(N(CC)CC)C>[C:18]1([C:17]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][N:6]=[C:5]3[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 224801043-Phenyl-1H-indazol-5-amine

Product 1

HCID 20789113Phenyl-n-(3-phenyl(1h-indazol-5-yl))carboxamideYield 8%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-amino-3-phenyl-1H-indazole (190 mg, 0.909 mmol) in acetonitrile (6 mL) was added benzoyl chloride (123 mg, 0.909 mmol). The solution was allowed to reflux for three hours. Triethylamine (3 drops) was added over a period of one hour while reflux continued for an additional hour. The solution was condensed and distilled water was added. The reaction mixture was extracted with ethyl acetate. The organics were dried using sodium sulfate, and condensed to give a solid. The solid was purified using chromatography (SiO2, 30–45% ethyl acetate/hexanes) to give the title compound (20 mg, 8% yield). 1H NMR (DMSO-d6) δ 13.40 (br s, 1H), 10.32 (s, 1H), 8.56 (s, 1H), 7.96 (m, 4H), 7.75 (d, 1H), 7.55 (m, 6H), 7.39 (t, 1H); ES-MS (m/z) 314 [M+1]+.

Workup

  1. temperatureto reflux for three hours
  2. temperaturewhile reflux
  3. waitcontinued for an additional hour
  4. customcondensed
  5. distillationdistilled water
  6. additionwas added
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. customThe organics were dried
  9. customsodium sulfate, and condensed
  10. customto give a solid
  11. customThe solid was purified

Sources & evidence

ORD record
ord-8a22183b44b04b3698131e56e42b66f9
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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