Triethylamine → 7-[4-(2-ethoxyethoxy)phenyl]-N-[4-[[methyl(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1$l^{6}-benzothiepine-4-carboxamide

HRID 1978689ノート

反応式

HRID 1978689 の反応式
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25](O)=[O:26])=[CH:18][C:17]=3[CH:28]=2)=[CH:9][CH:8]=1)[CH3:2].S(Cl)(Cl)=O.[CH3:33][N:34]([CH2:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1)[CH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.O>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:23])(=[O:24])[CH2:21][CH2:20][C:19]([C:25]([NH:46][C:45]4[CH:44]=[CH:43][C:42]([CH2:41][N:34]([CH3:33])[CH:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[CH:48][CH:47]=4)=[O:26])=[CH:18][C:17]=3[CH:28]=2)=[CH:11][CH:12]=1)[CH3:2]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 219958567-[4-(2-Ethoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

生成物 1

HCID 30093957-[4-(2-ethoxyethoxy)phenyl]-N-[4-[[methyl(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1$l^{6}-benzothiepine-4-carboxamide収率 44.4%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In THF (72 ml) was dissolved 7-[4-(2-ethoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (3.6 g). To the mixture were added under ice-cooling thionyl chloride (0.93 ml) and DMF (three drops), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added dropwise to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (2.23 g) and triethylamine (5.0 ml) in THF (67 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/ethanol=3/1) and recrystallized from ethanol to give 7-[4-(2-ethoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 84) (2.4 g).

後処理

  1. additionTo the mixture were added under ice-
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate/ethanol=3/1)
  8. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-77739fe31e9a4f7aa69a1d6f9beacfc9
出典データセット
uspto-grants-2001_05
特許番号
US06235771B1

反応ノート

読み込み中…