Diisopropylethylamine → HCID 70654233, compound

HRID 1405330Notes

Reaction equation

HRID 1405330 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](O)(=[O:29])=[O:28])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.CN.Cl.C[CH2:35][N:36](C(C)C)C(C)C>S(Cl)(Cl)=O.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][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]([NH:36][CH3:35])(=[O:29])=[O:28])[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 86670229HCID 86670229, compound

Product 1

HCID 70654233HCID 70654233, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (200 mg, 0.47 mmol, 1.00 equiv) in thionyl chloride (20 mL) was heated to reflux for 3 h in an oil bath. The resulting solution was concentrated in vacuo and the residue was diluted by 10 ml of dichloromethane. Then the resulting solution was added dropwise to a solution of MeNH2.HCl (318 mg, 4.75 mmol, 10.00 equiv) and DIEA (917 mg, 7.11 mmol, 15.00 equiv) in dichloromethane (20 mL) at 0° C., and then stirred overnight at room temperature, concentrated in vacuo, and 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 75% in 2.8 min, hold 75% in 2.2 min, up to 100% in 0.1 min, hold 100% in 0.5 min, down to 10% in 0.1 min); Detector, UV 254 nm. This resulted in 100 mg (49%) of 2,3-bis(4-methoxyphenyl)-N-methylquinoxaline-6-sulfonamide as a yellow solid.

Workup

  1. temperatureto reflux for 3 h in an oil bath
  2. concentrationThe resulting solution was concentrated in vacuo
  3. additionthe residue was diluted by 10 ml of dichloromethane
  4. concentrationconcentrated in vacuo
  5. custompurified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed))
  6. waitmobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 75% in 2.8 min
  7. customin 2.2 min
  8. waitup to 100% in 0.1 min
  9. customin 0.5 min
  10. waitdown to 10% in 0.1 min)
  11. customThis resulted in 100 mg (49%) of 2,3-bis(4-methoxyphenyl)-N-methylquinoxaline-6-sulfonamide as a yellow solid

Sources & evidence

ORD record
ord-4e57dc80fe1d49bb9e9c6403aebce1bc
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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