Potassium Carbonate → Ethyl [2-[2-[(5-cyano-2-methoxybenzenesulfonyl)-(2-methyl-1,3-thiazol-4-ylmethyl)amino)ethyl]-5-isopropylphenoxy]acetate

HRID 229599ノート

反応式

HRID 229599 の反応式
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17][NH:18][S:19]([C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=1[O:30][CH3:31])(=[O:21])=[O:20])[CH3:2].Cl.Cl[CH2:35][C:36]1[N:37]=[C:38]([CH3:41])[S:39][CH:40]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17][N:18]([S:19]([C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=1[O:30][CH3:31])(=[O:20])=[O:21])[CH2:35][C:36]1[N:37]=[C:38]([CH3:41])[S:39][CH:40]=1)[CH3:2]

参加物

7

反応物 4

HCID 11430Potassium Carbonate3 回HCID 516892Sodium BicarbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)3 回HCID 17856206Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate

生成物 1

HCID 86598015Ethyl [2-[2-[(5-cyano-2-methoxybenzenesulfonyl)-(2-methyl-1,3-thiazol-4-ylmethyl)amino)ethyl]-5-isopropylphenoxy]acetate収率 83.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A suspension of 300 mg of ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate, 132 mg of 4-chloromethyl-2-methyl-1,3-thiazole hydrochloride and 189 mg of potassium carbonate in 2.0 mL of N,N-dimethylformamide was stirred at room temperature for 18 hours, then at 50° C. for 3 hours. To the reaction mixture were added 60 mg of 4-chloromethyl-2-methyl-1,3-thiazole hydrochloride and 45 mg of potassium carbonate, and the mixture was stirred at the same temperature for 2.7 hours. To the reaction mixture were added 60 mg of 4-chloromethyl-2-methyl-1,3-thiazole hydrochloride and 45 mg of potassium carbonate, and the mixture was stirred at the same temperature for 3 hours. Furthermore, to the reaction mixture was added 2 mL of N,N-dimethylformamide, and the mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture were added water and saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, aqueous sodium chloride solution, and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 311 mg of ethyl[2-[2-[(5-cyano-2-methoxybenzenesulfonyl)-(2-methyl-1,3-thiazol-4-ylmethyl)amino]ethyl]-5-isopropylphenoxy]acetate.

後処理

  1. waitat 50° C. for 3 hours
  2. stirringthe mixture was stirred at the same temperature for 2.7 hours
  3. stirringthe mixture was stirred at the same temperature for 3 hours
  4. stirringthe mixture was stirred at the same temperature for 1.5 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water, aqueous sodium chloride solution, and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-acf30d2301e14481be58ddc554bad906
出典データセット
uspto-grants-2009_07
特許番号
US07563822B2

反応ノート

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