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

HRID 658478

反応式

HRID 658478 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 535108144-chloro-N-methoxy-N-methylpyridine-2-carboxamide収率 98%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bf6eaa704a24a61b72f12afc0af72b6
出典データセット
uspto-grants-2011_12
特許番号
US08076488B2

関連ノート

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