Benzo[b]thiophene-3-ethanamine → HCID 10045921, compound

HRID 392157

Reaction equation

HRID 392157 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH2:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.BrC1C=CC(S(O[CH2:24][C@@H:25]2[O:39][C:29]3=[C:30]4[C:35](=[CH:36][CH:37]=[C:28]3[O:27][CH2:26]2)[N:34]=[C:33]([CH3:38])[CH:32]=[CH:31]4)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CS(C)=O.O>[S:1]1[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([CH2:6][CH2:7][NH:8][CH2:24][CH:25]2[O:39][C:29]3=[C:30]4[C:35](=[CH:36][CH:37]=[C:28]3[O:27][CH2:26]2)[N:34]=[C:33]([CH3:38])[CH:32]=[CH:31]4)=[CH:5]1

Participants

6

Reactant 3

HCID 26743Benzo[b]thiophene-3-ethanamineHCID 516892Sodium BicarbonateHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

Product 1

HCID 10045921HCID 10045921, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-benzo[b]thiophen-3yl-ethylamine (354 mg, 2.0 mmol) in 1 mL of anhydrous DMSO was added [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromo-benzenesulfonate (300 mg, 0.67 mmol). The reaction mixture was stirred at ambient temperature for 4 days. The reaction was diluted with H2O (10 mL), poured into saturated aqueous sodium bicarbonate (25 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with 1:1 H2O/brine (40 mL) and brine (40 mL), then were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. Flash chromatography (2×20 cm SiO2, CH2Cl2 to 3% MeOH/CH2Cl2 gradient) afforded 225 mg (86%) of the (S)-enantiomer of the title compound as a thick oil. The fumarate salt was prepared by treating the amine in ethyl acetate with a solution of 66 mg (0.57 mmol) fumaric acid in methanol. The precipitated salt, a pale yellow solid, weighed 190 mg (m.p. 124-127° C.); MS (ESI) m/z 391 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed with 1:1 H2O/brine (40 mL) and brine (40 mL)
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-e5563d0d581b4f80ac23250d52eef666
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Linked notes

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