Triethylamine → 2-{3-Methyl-5-[({[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}amino)sulfonyl]-2-thienyl}ethyl acetate

HRID 1696779ノート

反応式

HRID 1696779 の反応式
[CH3:1][C:2]1[CH:6]=[C:5]([S:7](=[O:10])(=[O:9])[NH2:8])[S:4][C:3]=1[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15].[C:17]1([O:23]C(Cl)=O)C=CC=CC=1.C(N(CC)CC)C.[CH3:34][C:35]1[N:40]=[C:39]([NH2:41])[CH:38]=[C:37]([C:42]([F:45])([F:44])[F:43])[CH:36]=1>C(#N)C>[C:14]([O:13][CH2:12][CH2:11][C:3]1[S:4][C:5]([S:7]([NH:8][C:17](=[O:23])[NH:41][C:39]2[CH:38]=[C:37]([C:42]([F:45])([F:43])[F:44])[CH:36]=[C:35]([CH3:34])[N:40]=2)(=[O:10])=[O:9])=[CH:6][C:2]=1[CH3:1])(=[O:16])[CH3:15]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 184285216-Methyl-4-(trifluoromethyl)pyridin-2-amineHCID 67273589HCID 67273589、化合物

生成物 1

HCID 426288892-{3-Methyl-5-[({[6-methyl-4-(trifluoromethyl)pyridin-2-yl]carbamoyl}amino)sulfonyl]-2-thienyl}ethyl acetate収率 177.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 0.235 g acetic acid 2-(3-methyl-5-sulfamoyl-thiophen-2-yl)-ethyl ester in 5 ml acetonitrile was added 0.188 g phenylchloroformate and 0.252 g triethylamine at 0° C. and the mixture was stirred at this temperature for 2 h. To the resulting suspension was added 0.220 g 6-methyl-4-trifluoromethyl-pyridin-2-ylamine and the mixture was heated to 60C for 18 h. The reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine and evaporated. The residue was triturated with diethylether. The solid was collected by filtration to yield 0.736 g of the title compound as light yellow crystals. MS (ISN) M−H+=463.9

後処理

  1. customThe reaction mixture was partitioned between 10% citric acid and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. customevaporated
  5. customThe residue was triturated with diethylether
  6. filtrationThe solid was collected by filtration

出典と根拠

ORDレコード
ord-2f25da19c7c44a488f37b7adb7d47f92
出典データセット
uspto-grants-2012_04
特許番号
US08163778B2

反応ノート

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