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

HRID 524378Notes

Reaction equation

HRID 524378 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][N:25]([CH3:30])[S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[CH3:24][N:25]([CH3:30])[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 83372Dimethylsulphamoyl chlorideHCID 670349784-(3-Morpholin-4-yl-quinoxalin-6-yl)-phenylamine

Product 1

HCID 67035357N,N-dimethyl-N'-{4-[3-(morpholin-4-yl)quinoxalin-6-yl]phenyl}sulfuric diamideYield 52.6%

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 dimethylsulfamyl 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 (71 mg). 1H-NMR (300 MHz, d6-DMSO) δ=10.06 (1H, br s), 8.76 (1H, s), 7.84 (1H, d), 7.66-7.79 (4H, m)), 7.27 (2H, d), 3.72 (8H, s), 2.70 (6H, s).

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-6eb27508d5784ec98f66b9a00db5d108
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

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