Benzenesulfonamide, 3-amino- → HCID 78319766, compound

HRID 2280573Notes

Reaction equation

HRID 2280573 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:8]([C:17]([OH:19])=O)=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN1C(=O)CCC1.CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:8]([C:17]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([S:29](=[O:31])(=[O:30])[NH2:32])[CH:24]=3)=[O:19])=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729560HCID 86729560, compound

Product 1

HCID 78319766HCID 78319766, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-(4-fluorophenoxy)quinoxaline-2-carboxylic acid (28.42 mg, 0.1 mmol), 3-aminobenzenesulfonamide (20.7 mg, 0.12 mmol), HATU (38.0 mg, 0.10 mmol) and N-methylmorpholine (21.99 μL, 0.20 mmol) in NMP (0.5 mL) and DMSO (0.1 mL) was stirred at 25° C. for 16 hours. The reaction was filtered and purified by reverse phase HPLC using a gradient of 1-99% ACN in Water and HCl as a modifier. 3-(4-Fluorophenoxy)-N-(3-sulfamoylphenyl)quinoxaline-2-carboxamide (1) (13.9 mg, 32%) was obtained as a white solid. ESI-MS m/z calc. 438.08, found 439.5 (M+1)+; Retention time: 1.49 minutes (3 minutes run).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d4224b772668486d848cc49cbb455178
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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