Diisopropylethylamine → HCID 70654233, compound

HRID 2205158Notes

Reaction equation

HRID 2205158 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.C(Cl)Cl>[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, compoundYield 49%

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 under reflux for 3 h, then concentrated under vacuum. The residue was diluted with 10 ml of CH2Cl2 and added dropwise into a solution of MeNH2.HCl (318 mg, 4.75 mmol, 10.00 equiv) and DIEA (917 mg, 7.11 mmol, 15.00 equiv) in CH2Cl2 (20 mL) at 0° C. The resulting solution was stirred for overnight at room temperature, concentrated under vacuum, and purified by Prep-HPLC, yielding 100 mg (49%) of 2,3-bis(4-methoxyphenyl)-N-methylquinoxaline-6-sulfonamide as a yellow solid.

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationconcentrated under vacuum
  3. additionThe residue was diluted with 10 ml of CH2Cl2
  4. concentrationconcentrated under vacuum
  5. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-07e8d3c6f7be442fa6f69bb58c676f0b
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

Loading…