Methanesulfonyl chloride → N-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-methanesulfonamide

HRID 524376Notes

Reaction equation

HRID 524376 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][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[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]([NH:23][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:19][CH:18]=2)=[CH:12][CH:11]=3)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 670349784-(3-Morpholin-4-yl-quinoxalin-6-yl)-phenylamine

Product 1

HCID 67035522N-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-methanesulfonamideYield 56.6%

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 methane sulfonyl 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 triturated with dichloromethane and filtered to give the title compound (71 mg). UPLC-MS: RT=0.97 min; m/z (ES+) 385.19 [MH+]; required MW=384.46.

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 triturated with dichloromethane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f7e53d73adde4720bcccd5ae72430ffb
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

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