Methyl Isocyanate → N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-[methylaminocarbonyl]aminoethyl) methanesulphonamide

HRID 1458560Notes

Reaction equation

HRID 1458560 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1[C:7]([N:21]([CH2:26][CH2:27][NH2:28])[S:22]([CH3:25])(=[O:24])=[O:23])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2>ClCCl>[Cl:5][C:6]1[C:7]([N:21]([CH2:26][CH2:27][NH:28][C:3]([NH:2][CH3:1])=[O:4])[S:22]([CH3:25])(=[O:24])=[O:23])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 54554464HCID 54554464, compound

Product 1

HCID 22097020N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-[methylaminocarbonyl]aminoethyl) methanesulphonamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylisocyanate (8.2 μl, 8.0 mg, 0.14 mmol) was added to a solution of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-aminoethyl)-methanesulphonamide (from Preparation 27, 50 mg, 0.127 mmol) in dichloromethane (2 ml) at room temperature under nitrogen. After 30 minutes the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and concentrated under reduced pressure to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-[methylaminocarbonyl]aminoethyl) methanesulphonamide as a pale yellow foam (52 mg, 91%).

Workup

  1. concentrationAfter 30 minutes the mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-790b989a9e4544fb98a0035504d2b89e
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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