Triethylamine → HCID 86718147, compound

HRID 2205165Notes

Reaction equation

HRID 2205165 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]([OH:29])=O)[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1)[CH3:2].Cl.[CH3:31][O:32][NH2:33].CCN(CC)CC>S(Cl)(Cl)=O.C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]([NH:33][O:32][CH3:31])=[O:29])[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86718148HCID 86718148, compound

Product 1

HCID 86718147HCID 86718147, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2,3-bis(4-ethylphenyl)quinoxaline-6-carboxylic acid (150 mg, 0.39 mmol, 1.00 equiv) in thionyl chloride (20 mL) was heated under reflux for 3 h in a oil bath. The resulting solution was concentrated under vacuum and diluted with 20 ml of CH2Cl2. The resulting solution was added to a solution of O-methyl-hydroxylamine hydrochloride (326 mg, 3.93 mmol, 10.00 equiv) and NEt3 (396 mg, 3.92 mmol, 10.00 equiv) in CH2Cl2 (20 mL) at 0° C. and stirred overnight at room temperature. The reaction mixture was concentrated under vacuum, and the crude product (100 mg) was purified by Prep-HPLC yielding 15 mg (7%) of 2,3-bis(4-ethylphenyl)-N-methoxyquinoxaline-6-carboxamide as a white solid.

Workup

  1. temperatureunder reflux for 3 h in a oil bath
  2. concentrationThe resulting solution was concentrated under vacuum
  3. additiondiluted with 20 ml of CH2Cl2
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. customthe crude product (100 mg) was purified by Prep-HPLC

Sources & evidence

ORD record
ord-e2dc942f86e14f61a99f5926d702ab96
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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