HCID 10987666, compound → HCID 10002689, compound

HRID 1454315Notes

Reaction equation

HRID 1454315 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 10002689HCID 10002689, compoundYield 137.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a6c7c82d36ea470aab5812690dfe8cb1
Source dataset
uspto-grants-2009_01
Patent number
US07479500B2

Reaction notes

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