Water → HCID 22097042, compound

HRID 1458573Notes

Reaction equation

[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]([CH3:13])[CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([O:16][CH3:17])[C:6]([O:14][CH3:15])=[N:7]2.[CH2:18]([S:20](Cl)(=[O:22])=[O:21])[CH3:19].N1C=CC=CC=1.O>O1CCCC1>[CH3:15][O:14][C:6]1[C:5]([O:16][CH3:17])=[N:4][C:3]2[C:8](=[CH:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:2]=2[NH:1][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[N:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 5-amino-2,3-dimethoxy-6,7-dimethylquinoxaline (from Preparation 2) (50 mg, 0.214 mmol), ethanesulphonyl chloride (138 mg, 1.07 mmol) and pyridine (87 μl, 1.07 mmol) in dry tetrahydrofuran (1 ml) was stirred at 20° C. for 3.5 hours. Additional portions of ethanesulphonyl chloride (138 mg, 1.07 mmol) and pyridine (87 ml, 1.07 mmol) were added and the mixture was stirred for a further 4 days. Water (0.6 ml) was added, and the mixture was stirred for 40 minutes. The mixture was partitioned between ethyl acetate (15 ml) and 2M hydrochloric acid (5 ml). The organic solution was washed with water (5 ml), saturated aqueous sodium bicarbonate (5 ml), dried (MgSO4), and concentrated under reduced pressure to give the title compound (67 mg, 96%) as a straw-coloured solid, m.p. 201°-203° C.

Workup

stirringthe mixture was stirred for a further 4 days
stirringthe mixture was stirred for 40 minutes
customThe mixture was partitioned between ethyl acetate (15 ml) and 2M hydrochloric acid (5 ml)
washThe organic solution was washed with water (5 ml), saturated aqueous sodium bicarbonate (5 ml)
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-71605d3dce5549df8c309e5ca67f473b
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852016

Reaction notes

Loading…