1,2-Dichloroethane → HCID 86681758, compound

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Reaction Steps

A mixture of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.174 g, 0.415 mmol), 2-(5-((N-(2-morpholinoethyl)methylsulfonamido)methyl)-1,3-dioxoisoindolin-2-yl)acetic acid 2,2,2 trifluoroacetic acid salt (0.224 g, 0.415 mmol), EDC (0.239 g, 1.246 mmol), and DMAP (0.101 g, 0.830 mmol) in DCM (10 ml) was stirred at room temperature for 3 hours. The mixture was diluted with DCM and washed with 0.5N HCl, aqueous 5% NaHCO3 and brine; the organic phase was dried over sodium sulfate; and the solvent removed under vacuum. The crude was purified by filtration through a silica cartridge (DCM:MeOH=98:2); a further purification by flash chromatography on silica gel column (DCM:MeOH=99=1) was performed to afford S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(5-((N-(2-morpholinoethyl)methylsulfonamido)methyl)-1,3-dioxoisoindolin-2-yl)acetoxy)ethyl)pyridine 1-oxide (0.125 g, 0.151 mmol, 36.4% yield, MS/ESI+ 827.03 [MH]+, [αD]=−28.63, c=0.8, DCM). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.44 (s, 2H), 7.70-8.09 (m, 3H), 7.19 (d, 1H), 7.03-7.13 (m, 1H), 6.96 (dd, 1H), 7.08 (t, 1H), 6.02 (dd, 1H), 4.59 (s, 2H), 4.21-4.52 (m, 2H), 3.75-4.03 (m, 2H), 3.44-3.54 (m, 4H), 3.30-3.44 (m, 3H), 3.17-3.23 (m, 1H), 3.12 (s, 3H), 2.37 (t, 2H), 2.16-2.32 (m, 4H), 1.13-1.33 (m, 1H), 0.48-0.72 (m, 2H), 0.16-0.48 (m, 2H)

Provenance & Evidence