HCID 10987666, 화합물 → HCID 10002689, 화합물

HRID 1454315노트

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HRID 1454315 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 10002689HCID 10002689, 화합물수율 137.8%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a6c7c82d36ea470aab5812690dfe8cb1
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07479500B2

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