HCID 10987666、化合物 → HCID 10002689、化合物

HRID 1454315ノート

反応式

HRID 1454315 の反応式
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:26][C:16]3=[C:17]4[C:22](=[CH:23][CH:24]=[C:15]3[O:14][CH2:13]2)[N:21]=[C:20]([CH3:25])[CH:19]=[CH:18]4)(=O)=O)=CC=1.[S:28]1[C:32]([C:33]2[CH2:34][CH2:35][NH:36][CH2:37][CH:38]=2)=[CH:31][C:30]2[CH:39]=[CH:40][CH:41]=[CH:42][C:29]1=2>CS(C)=O>[S:28]1[C:32]([C:33]2[CH2:34][CH2:35][N:36]([CH2:11][CH:12]3[O:26][C:16]4=[C:17]5[C:22](=[CH:23][CH:24]=[C:15]4[O:14][CH2:13]3)[N:21]=[C:20]([CH3:25])[CH:19]=[CH:18]5)[CH2:37][CH:38]=2)=[CH:31][C:30]2[CH:39]=[CH:40][CH:41]=[CH:42][C:29]1=2

参加物

4

反応物 2

HCID 10987666HCID 10987666、化合物HCID 11280604(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate

生成物 1

HCID 10002689HCID 10002689、化合物収率 137.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

To a mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-toluenesulfonate (0.638 g, 1.66 mmol) and 4-benzo[b]thiophen-2-yl-1,2,3,6-tetrahydro-pyridine (0.46 g, 2.1 mmol) was added 12 mL of dimethylsulfoxide. The mixture was stirred at 90° C. for 18 hours. The solvent was evaporated under reduced pressure. The residue was partitioned between 500 mL each of methylene chloride and saturated aqueous sodium bicarbonate. The methylene chloride layer was washed with water twice and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave 0.98 g of oil. This was chromatographed on silica gel with a gradient of ethyl acetate and hexane. The product fractions were collected and concentrated in vacuum to give 0.39 g of the title compound as nearly pure, light yellow oil. This was triturated with ethanol to give 0.2563 g of the S enantiomer of the title compound as a light yellow solid, m.p. 174-176° C.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between 500 mL each of methylene chloride and saturated aqueous sodium bicarbonate
  3. washThe methylene chloride layer was washed with water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-a6c7c82d36ea470aab5812690dfe8cb1
出典データセット
uspto-grants-2009_01
特許番号
US07479500B2

反応ノート

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