Pyridine → N-methoxy-N-methylquinoxaline-6-carboxamide

HRID 1865431Notes

Reaction equation

HRID 1865431 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](Cl)=[O:12])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].N1C=CC=CC=1>C(Cl)Cl>[CH3:18][O:17][N:16]([CH3:15])[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[N:4]2)=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2776328Quinoxaline-6-carbonyl chloride

Product 1

HCID 59208155N-methoxy-N-methylquinoxaline-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate from step B (484 mg, 2.51 mmol) in 17 mL anhydrous methylene chloride cooled to 0° C. was added N,O-dimethylhydroxylamine hydrochloride (368 mg, 3.77 mmol) followed by pyridine (0.61 mL, 7.54 mmol). The reaction was warmed to room temperature and stirred overnight after which it was quenched with water. The aqueous layer was extracted with methylene chloride (2×) and the combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography using 40% EtOAc/Hexanes to give the product as a colorless oil. 1H NMR (CDCl3, 500 MHz): 3.45 (d, J=2.5 Hz, 3H), 3.59 (d, J=2.5 Hz, 3H), 8.05 (m, 1H), 8.15 (dd, J=8.7, 3.2 Hz, 1H), 8.46 (d, J=1.8 Hz, 1H), 8.91 (d, J=2.5, 2H). LC-MS: 1.11 min. (M+H)=111.

Workup

  1. customwas quenched with water
  2. extractionThe aqueous layer was extracted with methylene chloride (2×)
  3. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-1041eb7a6c4a4147ac9cb9a534451fa2
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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