Water → HCID 54183663, compound

HRID 343803Notes

Reaction equation

HRID 343803 reaction equation
N1C=CC=CC=1.[CH3:7][S:8]([O:11]S(C)(=O)=O)(=O)=[O:9].[NH2:16][C:17]1[C:26]([Cl:27])=[C:25]([CH3:28])[CH:24]=[C:23]2[C:18]=1[N:19]=[C:20]([O:31][CH3:32])[C:21]([O:29][CH3:30])=[N:22]2.O>O1CCCC1.C(OCC)(=O)C>[Cl:27][C:26]1[C:17]([NH:16][S:8]([CH3:7])(=[O:11])=[O:9])=[C:18]2[C:23](=[CH:24][C:25]=1[CH3:28])[N:22]=[C:21]([O:29][CH3:30])[C:20]([O:31][CH3:32])=[N:19]2

Participants

7

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 81560Methanesulfonic anhydride2×HCID 22614878HCID 22614878, compound

Product 1

HCID 54183663HCID 54183663, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (80 μl, 78 mg, 0.985 mmol) and methanesulphonic anhydride (172 mg, 0.985 mmol) were added to a solution of 5-amino-6-chloro-2,3-dimethoxy-7-methylquinoxaline (Example 3 step (e), 50 mg, 0.197 mmol) in dry tetrahydrofuran (1.6 ml) at room temperature under nitrogen. After stirring for 24 hours further pyridine (32 μl, 31 mg, 0.394 mmol) and methanesulphonic anhydride (69 mg, 0.394 mmol) were added. After a further 16 hours water (0.6 ml) was added and stirring continued for 1 hour. The mixture was diluted with ethyl acetate (15 ml) and washed with 2M hydrochloric acid (5 ml), water (5 ml), saturated sodium bicarbonate solution (5 ml) and brine (5 ml) and then dried (MgSO4), filtered and concentrated under reduced pressure. The solid residue was purified by flash chromatography on silica gel eluting with 3:1 hexane:ethyl acetate to give N-(6-chloro-2,3-dimethoxy-7-methylquinoxalin-5-yl)methanesulphonamide (55 mg, 84%) as a white solid mp 198° C.

Workup

  1. additionwere added
  2. washwashed with 2M hydrochloric acid (5 ml), water (5 ml), saturated sodium bicarbonate solution (5 ml) and brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solid residue was purified by flash chromatography on silica gel eluting with 3:1 hexane

Sources & evidence

ORD record
ord-1e13e93ec4c84923a1ef694e41f091c5
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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