[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate → HCID 10387289, compound

HRID 392156Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][NH2:15])[C:7]=2[CH:6]=[CH:5][CH:4]=1.BrC1C=CC(S(O[CH2:27][C@@H:28]2[O:42][C:32]3=[C:33]4[C:38](=[CH:39][CH:40]=[C:31]3[O:30][CH2:29]2)[N:37]=[C:36]([CH3:41])[CH:35]=[CH:34]4)(=O)=O)=CC=1>CS(C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][NH:15][CH2:27][CH:28]3[O:42][C:32]4=[C:33]5[C:38](=[CH:39][CH:40]=[C:31]4[O:30][CH2:29]3)[N:37]=[C:36]([CH3:41])[CH:35]=[CH:34]5)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3-(7-methoxy-benzofuran-3-yl)-propylamine (770 mg, 3.75 mmol) in 5 mL of anhydrous DMSO was added [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (563 mg, 1.25 mmol). The reaction mixture was heated to 50° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (3×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. Flash chromatography on SiO2 (5% MeOH/CH2Cl2) afforded 120 mg (23%) of the (S)-enantiomer of the title compound as a yellow oil. The fumarate salt was prepared, yielding 132 mg of a beige solid, m.p. 155-160° C.; MS (ESI) m/z 419 [M+H]+.

Workup

extractionextracted with ethyl acetate (3×10 mL)
washThe combined organic layers were washed with brine (3×30 mL)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-d69b73bc8d314f61af7b9f2f23a3971c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800637B2

Reaction notes

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