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

HRID 1272738

반응식

HRID 1272738 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 6342Acetonitrile용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-21ffdbc5cd51486486fac2ac3ff28473
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208513B2

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