4-Toluenesulfonyl chloride → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-cyclohexyl-1,3,4-oxadiazole-2-carboxamide

HRID 58705노트

반응식

HRID 58705 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:18])[C:15]([OH:17])=O.S(Cl)(Cl)=O.ClC1C=C2C(=CC=1)NC=C2CCNC(=O)C(Cl)=O.C(N(CC)CC)C.[CH:48]1([C:54]([NH:56][NH2:57])=O)[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:15]1[O:17][C:54]([CH:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)=[N:56][N:57]=1)=[O:18]

참가 물질

9

반응물 6

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 240039CyclohexanecarbohydrazideHCID 668319752-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acidHCID 866638412-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetyl chloride

생성물 1

HCID 66831875N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-cyclohexyl-1,3,4-oxadiazole-2-carboxamide수율 1.5%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매3회

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온도
80 °C

실험 절차

To a suspension of 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid (0.920 mg; 3.45 mmol) in chloroform (50 mL) was added thionyl chloride (2.51 mL; 34.50 mmol) and the mixture was stirred at 80° C. for 3 h and was then evaporated to dryness. The resulting 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetyl chloride (0.480 g; 1.68 mmol) was dissolved in dichloromethane (12 mL) and a mixture of triethylamine (0.945 mL; 6.73 mmol) and cyclohexanecarboxylic acid hydrazide (0.232 g; 1.60 mmol) in dichloromethane (8 mL) was added at 0° C. The mixture was stirred at room temperature for 2 h and p-toluenesulfonyl chloride (0.324 g, 1.68 mmol) was added. The resulting mixture was stirred overnight at room temperature, diluted with dichloromethane, washed with an aqueous solution of sodium carbonate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluent: 12 to 100% ethyl acetate in heptane) to give 0.0088 g (1.40%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-cyclohexyl-1,3,4-oxadiazole-2-carboxamide as a white solid.

후처리

  1. customwas then evaporated to dryness
  2. additionwas added at 0° C
  3. stirringThe mixture was stirred at room temperature for 2 h
  4. stirringThe resulting mixture was stirred overnight at room temperature
  5. washwashed with an aqueous solution of sodium carbonate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (eluent: 12 to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-ec42d7ad6f884722a67acfa8e4f09825
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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