[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 10070877, compound

HRID 392166Notes

Reaction equation

HRID 392166 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.[F:28][C:29]1[CH:41]=[CH:40][C:32]2[S:33][CH:34]=[C:35]([CH2:36][CH2:37][CH2:38][NH2:39])[C:31]=2[CH:30]=1>CS(C)=O.C(=O)(O)[O-].[Na+]>[F:28][C:29]1[CH:41]=[CH:40][C:32]2[S:33][CH:34]=[C:35]([CH2:36][CH2:37][CH2:38][NH:39][CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[C:31]=2[CH:30]=1

Participants

5

Reactant 2

HCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonateHCID 22662943HCID 22662943, compound

Product 1

HCID 10070877HCID 10070877, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (151 mg, 0.669 mmol) and 3-(5-fluoro-benzo[b]thiophen-3-yl)-propylamine (140 mg, 0.335 mmol) in anhydrous dimethylsulfoxide (7 mL) was stirred at ambient temperature for three days without any apparent reaction occurring. The reaction was then heated at 40° C. for two days, resulting in complete conversion. The cooled reaction was diluted with saturated aqueous sodium bicarbonate (35 mL) and extracted with ethyl acetate (3×35 mL). The combined organic layers were washed with brine (40 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacua. Flash chromatography on silica gel (2/2/96 methanol/2 M ammonia in methanol/methylene chloride) afforded 90 mg (63%) of the title compound as a yellow viscous oil, which was converted to its fumarate salt as a yellow solid: mp 117-120° C.; MS (ES) m/z 423 [M+H]+; [α]D −29.1° (c 0.94, DMSO)

Workup

  1. temperatureThe reaction was then heated at 40° C. for two days
  2. customresulting in complete conversion
  3. customThe cooled reaction
  4. extractionextracted with ethyl acetate (3×35 mL)
  5. washThe combined organic layers were washed with brine (40 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacua

Sources & evidence

ORD record
ord-6fd0a8189f8f41b9bf795009e9007d2f
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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