Dimethylformamide → 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(2-pyridinylsulfanyl)phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 856472ノート

反応式

HRID 856472 の反応式
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28](O)=[O:29])=[CH:20][C:19]=3[CH:31]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].CN(C=O)C.S(Cl)(Cl)=O.[N:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[S:47][C:48]1[CH:54]=[CH:53][C:51]([NH2:52])=[CH:50][CH:49]=1>C1COCC1.O.C(N(CC)CC)C>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28]([NH:52][C:51]4[CH:53]=[CH:54][C:48]([S:47][C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=5)=[CH:49][CH:50]=4)=[O:29])=[CH:20][C:19]=3[CH:31]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 114301667-[4-(2-Butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 189716604-[(Pyridin-2-yl)sulfanyl]aniline

生成物 1

HCID 695213307-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(2-pyridinylsulfanyl)phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide収率 39.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

7-[4-(2-butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (1.0 g) was dissolved in THF (20 ml), DMF (2 droplets) was added to the mixture, and thionyl chloride (0.34 ml) was added to the mixture. The mixture was stirred at room temperature for 1 hour, and the mixture was added dropwise to the solution of 4-(2-pyridinylsulfanyl) aniline (0.53 g) and triethylamine (1.97 ml) in THF (20 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(2-pyridinylsulfanyl)phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 182) (0.57 g).

後処理

  1. additionwas added to the mixture
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-afcf712e7bc440dfbf4042756b284c11
出典データセット
uspto-grants-2007_08
特許番号
US07262185B2

反応ノート

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