[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 44220113, compound

HRID 860006Notes

Reaction equation

HRID 860006 reaction equation
BrC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[CH3:28][C@@H:29]1[NH:34][CH2:33][CH2:32][N:31]([C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=2)[CH2:30]1>CS(C)=O.C(=O)(O)[O-].[Na+]>[CH3:26][C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14][C@H:13]([CH2:12][N:34]4[CH2:33][CH2:32][N:31]([C:35]5[CH:44]=[CH:43][C:42]6[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=6)[N:36]=5)[CH2:30][C@@H:29]4[CH3:28])[O:27][C:17]3=2)[N:22]=1

Participants

5

Reactant 2

HCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonateHCID 44220319HCID 44220319, compound

Product 1

HCID 44220113HCID 44220113, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (0.165 g, 0.367 mmol) and (S)-2-(3-methyl-piperazin-1-yl)-quinoline (250 mg, 1.10 mmol) in anhydrous dimethylsulfoxide (4 mL) was heated at 50° C. overnight. The cooled reaction was diluted with saturated aqueous sodium bicarbonate (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography on silica gel (2/2/96 methanol/2 M ammonia in methanol/methylene chloride) afforded 100 mg (62%) of the title compound as an off-white solid: mp 141–144° C.; MS (ES) m/z 441 [M+H]+; [α]D −36.5° (c 1.0, DMSO).

Workup

  1. customThe cooled reaction
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f7080a04c9845cf98088c6196e61e27
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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