Triethylamine → 5-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide

HRID 1374168노트

반응식

HRID 1374168 반응식
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.Cl.[CH3:13][O:14][NH:15][CH3:16].ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8]([N:15]([O:14][CH3:13])[CH3:16])=[O:9])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 181649HOAtHCID 210758725-Bromo-3-fluoropyridine-2-carboxylic acid

생성물 1

HCID 210758695-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of crude 5-bromo-3-fluoropyridine-2-carboxylic acid (40.65 g, 184.8 mmol), O,N-dimethylhydroxylamine hydrochloride (21.63 g, 221.7 mmol), 1-ethyl-(3-dimethyl-aminopropyl)-carbodiimide hydrochloride (70.85 g, 369.6 mmol), 1-hydroxy-7-azabenzotriazole (2.497 g, 18.48 mmol), and triethylamine (16.48 mL, 118.3 mmol) in 200 mL DMF was stirred at room temperature overnight. The solution was partially concentrated in vacuo and partitioned between ethyl acetate and 10% aqueous sodium bicarbonate. The aqueous layer was extracted 4× with ethyl acetate, and the combined organics were washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum to provide 5-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 263.01 for M+H+(79Br).

후처리

  1. concentrationThe solution was partially concentrated in vacuo
  2. custompartitioned between ethyl acetate and 10% aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted 4× with ethyl acetate
  4. washthe combined organics were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-1c16b7dd319748288a7b04a8f4712977
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163951B2

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