Triethylamine → 4-chloro-N-methoxy-N-methylpyridine-2-carboxamide

HRID 658478

반응식

HRID 658478 반응식
Cl.[CH3:2][N:3](C)[OH:4].[CH2:6](N(CC)CC)C.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21](Cl)=[O:22])[CH:16]=1>C1COCC1.C(#N)C>[Cl:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]([N:3]([O:4][CH3:6])[CH3:2])=[O:22])[CH:16]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

생성물 1

HCID 535108144-chloro-N-methoxy-N-methylpyridine-2-carboxamide수율 98%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a mixture of dimethylhydroxylamine HCl (510 mg, 5.18 mmol) and triethylamine (2.16 mL, 15.5 mmol) in anhydrous THF (9.41 mL) and acetonitrile (2.35 mL) was added 4-chloropyridine-2-carbonyl chloride hydrochloride (1.00 g, 4.71 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h then at RT for 16 h. The solvent was removed under reduced pressure and partitioned between EtOAc and water. The organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by MPLC (biotage) eluted with 30% EtOAc/Hex to afford 925 mg (98%) of 4-chloro-N-methoxy-N-methylpyridine-2-carboxamide as an orange oil: TLC (50% EtOAc/Hex), Rf=0.31.

후처리

  1. waitat RT for 16 h
  2. customThe solvent was removed under reduced pressure
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by MPLC (biotage)
  8. washeluted with 30% EtOAc/Hex

출처 및 근거

ORD 기록
ord-8bf6eaa704a24a61b72f12afc0af72b6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076488B2

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