Methanamine, N-methoxy-, hydrochloride (1:1) → 3-Chloro-N-methoxy-N-methylpyrazine-2-carboxamide

HRID 573310ノート

反応式

HRID 573310 の反応式
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[C:3]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1

参加物

5

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 15019003-Chloro-2-pyrazine-carboxylic acid

生成物 1

HCID 534175293-Chloro-N-methoxy-N-methylpyrazine-2-carboxamide収率 43.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3-chloropyrazine-2-carboxylic acid (5.46 g) in THF (100 mL) was added CDT (6.14 g) at room temperature, and the mixture was stirred at room temperature for 30 min and heated to 50° C. After stirring at 50° C. for 1 h, the mixture was cooled to room temperature. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (5.04 g) and DIPEA (9.02 mL) at room temperature, and the mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (3.05 g).

後処理

  1. additionwas added CDT (6.14 g) at room temperature
  2. temperatureheated to 50° C
  3. stirringAfter stirring at 50° C. for 1 h
  4. temperaturethe mixture was cooled to room temperature
  5. stirringthe mixture was stirred at room temperature overnight
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-e505fdd13f504d33934ab3852f3f9bd8
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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