Dimethylformamide → HCID 70654224, compound

HRID 1405331Notes

Reaction equation

HRID 1405331 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.S(Cl)(Cl)=O.CN(C)C=O.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>ClCCl.C1(C)C=CC=CC=1>[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]([N:40]4[CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)(=[O:28])=[O:29])[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 86670229HCID 86670229, compound

Product 1

HCID 70654224HCID 70654224, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-bis(4-methoxyphenyl)quinoxaline-6-sulfonic acid (350 mg, 0.83 mmol, 1.00 equiv), thionyl chloride (1.0 g, 8.40 mmol, 10.00 equiv), N,N-dimethylformamide (60 mg, 0.82 mmol, 1.00 equiv) and toluene (10 mL) was heated to reflux for 3 h in an oil bath. The resulting mixture was concentrated in vacuo and diluted with 10 ml of dichloromethane. Then the resulting mixture was added into a solution of morpholine (1.44 g, 16.53 mmol, 20.00 equiv) in dichloromethane (10 mL) at 0° C. The reaction mixture was 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 80% in 3 min, hold 80% in 2 min, up to 100% in 0.1 min, hold 100% in 0.9 min); Detector, UV 254 nm. This resulted in 60 mg (34%) of 4-(2,3-bis(4-methoxyphenyl)quinoxalin-6-ylsulfonyl)morpholine as a white solid.

Workup

  1. temperatureto reflux for 3 h in an oil bath
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. additiondiluted with 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 80% in 3 min
  7. customin 2 min
  8. waitup to 100% in 0.1 min
  9. customin 0.9 min
  10. customThis resulted in 60 mg (34%) of 4-(2,3-bis(4-methoxyphenyl)quinoxalin-6-ylsulfonyl)morpholine as a white solid

Sources & evidence

ORD record
ord-073a79782daf4ef98c0fbc7230fd45b1
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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