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

HRID 58704

反応式

HRID 58704 の反応式
[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.[C:48]1([CH2:54][C:55]([NH:57][NH2:58])=O)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.ClCCl>[CH2:54]([C:55]1[O:17][C:15]([C:14]([NH:13][CH2:12][CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][CH:6]=2)=[O:18])=[N:58][N:57]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

参加物

9

反応物 6

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 70301Benzeneacetic acid, hydrazideHCID 668319752-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acidHCID 866638412-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetyl chloride

生成物 1

HCID 668318505-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1,3,4-oxadiazole-2-carboxamide収率 2.6%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
80 °C

実験手順

To a suspension of 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid (0.350 mg; 1.31 mmol) in chloroform (20 mL) was added thionyl chloride (0.955 mL; 13.12 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 (0.180 g, 0.631 mmol) was dissolved in dichloromethane (12 mL) and a mixture of triethylamine (0.355 mL; 2.53 mmol) and 2-phenylacetic acid hydrazide (0.092 g; 0.600 mmol) in dichloromethane (2 mL) was added at 0° C. The mixture was stirred at room temperature for 3 days and p-toluenesulfonyl chloride (0.122 g, 0.631 mmol) was added. The resulting mixture was stirred 18 h 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 0.006 g (2.5%) of 5-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1,3,4-oxadiazole-2-carboxamide as a white solid.

後処理

  1. customwas then evaporated to dryness
  2. additionwas added at 0° C
  3. stirringThe mixture was stirred at room temperature for 3 days
  4. stirringThe resulting mixture was stirred 18 h 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)

出典と根拠

ORDレコード
ord-d9f9d46efcd24e76a5e4ba5bce750045
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

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