N-Methylsulfamoyl chloride → N-methyl-N'-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuric diamide

HRID 524379Notes

Reaction equation

HRID 524379 reaction equation
[N:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:24][NH:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[CH3:24][NH:25][S:26](=[O:28])(=[O:27])[NH:23][C:20]1[CH:21]=[CH:22][C:17]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[N:16]3)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11789235N-Methylsulfamoyl chlorideHCID 670349784-(3-Morpholin-4-yl-quinoxalin-6-yl)-phenylamine

Product 1

HCID 67035764N-methyl-N'-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuric diamideYield 23%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of 4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine [Intermediate Example 4.1] (100 mg) and pyridine (0.5 mL) was treated with a solution of methylsulfamyl chloride (75 mg, 0.65 mmol) in pyridine (0.6 mL) and stirred at room temperature overnight. The reaction was partitioned between dichloromethane and water, the phases separated and the organic layer concentrated in vacuo. The residue was purified by preparative reverse phase HPLC to give the title compound (30 mg), contaminated by ca. 20% formic acid.

Workup

  1. customThe reaction was partitioned between dichloromethane and water
  2. customthe phases separated
  3. concentrationthe organic layer concentrated in vacuo
  4. customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-34eb2898dd5a4cae935846d2bdb50a70
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

Loading…