Dimethylformamide → HCID 70654232, compound

HRID 1405329Notes

Reaction equation

HRID 1405329 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:27]([OH:30])(=O)=[O:28])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.C[N:32](C)C=O>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:27]([NH2:32])(=[O:30])=[O:28])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86670229HCID 86670229, compound

Product 1

HCID 70654232HCID 70654232, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (137.2 mg, 0.33 mmol, 1.00 equiv) in thionyl chloride (12 mL) was added N,N-dimethylformamide (2 mL) dropwise with stifling. The mixture was stirred at reflux for 3 hr in an oil bath. The resulting mixture was concentrated in vacuo. The residue was dissolved in acetonitrile (10 mL) and added to a solution of ammonia (2 g) in acetonitrile (10 mL) dropwise at 0° C. The resulting mixture was stirred overnight at room temperature, then concentrated in vacuo. The crude product (100 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed)): Column, SunFire Prep C18, 5 um, 19*100 mm; mobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 65% in 2.8 min, hold 65% in 2.5 min, up to 100% in 0.1 min, hold 100% in 0.6 min, down to 10% in 0.1 min); Detector, UV 254 nm. This resulted in 16 mg (12%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonamide as a light yellow solid.

Workup

  1. temperatureat reflux for 3 hr in an oil bath
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in acetonitrile (10 mL)
  4. additionadded to a solution of ammonia (2 g) in acetonitrile (10 mL) dropwise at 0° C
  5. stirringThe resulting mixture was stirred overnight at room temperature
  6. concentrationconcentrated in vacuo
  7. customThe crude product (100 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed))
  8. customin 2.5 min
  9. waitup to 100% in 0.1 min
  10. customin 0.6 min
  11. waitdown to 10% in 0.1 min)
  12. customThis resulted in 16 mg (12%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonamide as a light yellow solid

Sources & evidence

ORD record
ord-365cdef2758d46b9b8cbc094ca4cc1f4
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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