Cesium carbonate → HCID 78319770, compound

HRID 2280575Notes

Reaction equation

HRID 2280575 reaction equation
Cl[C:2]1[C:3]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([S:21](=[O:24])(=[O:23])[NH2:22])[CH:16]=2)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[OH:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[F:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[O:33][C:2]1[C:3]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([S:21](=[O:24])(=[O:23])[NH2:22])[CH:16]=2)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 86729561HCID 86729561, compound

Product 1

HCID 78319770HCID 78319770, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-N-(3-sulfamoylphenyl)quinoxaline-2-carboxamide (54.4 mg, 0.15 mmol) in N-methylpyrrolidinone (1 mL) was added 2,4-difluorophenol (19.5 mg, 0.15 mmol) and cesium carbonate (146.6 mg, 0.45 mmol) and the reaction was stirred at 100° C. for 25 minutes. The reaction was filtered and purified by reverse phase preparative chromatography utilizing a gradient of 10-99% acetonitrile in water containing HCl as a modifier to yield 3-(2,4-difluorophenoxy)-N-(3-sulfamoylphenyl)quinoxaline-2-carboxamide (5) (13.2 mg, 19%). ESI-MS m/z calc. 456.07, found 457.3 (M+1)+; Retention time: 1.76 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 11.32 (s, 1H), 8.47-8.37 (m, 1H), 8.27-8.15 (m, 1H), 7.97-7.75 (m, 4H), 7.69-7.50 (m, 4H), 7.45 (s, 2H), 7.30-7.17 (m, 1H) ppm.

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase preparative chromatography
  3. additioncontaining HCl as a modifier

Sources & evidence

ORD record
ord-2de575b9faa24db2bf27246cc77ff354
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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