Chlorosuccinimide → 3-({[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]amino}carbonyl)-N-hydroxy-5-(5-methyl-2-pyridinyl)benzenecarboximidoyl chloride

HRID 1257544ノート

反応式

HRID 1257544 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:28])[C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[CH:15]=[C:14](/[CH:25]=[N:26]/[OH:27])[CH:13]=2)[CH3:9])=[N:6][CH:7]=1.[Cl:29]N1C(=O)CCC1=O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11]([C:12]2[CH:13]=[C:14]([C:25]([Cl:29])=[N:26][OH:27])[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[CH:17]=2)=[O:28])[CH3:9])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 87195802N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-[(E)-hydroxyiminomethyl]-5-(5-methyl-2-pyridinyl)benzamide

生成物 1

HCID 866496473-({[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]amino}carbonyl)-N-hydroxy-5-(5-methyl-2-pyridinyl)benzenecarboximidoyl chloride収率 103.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a solution of N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-[(E)-(hydroxyimino)methyl]-5-(5-methyl-2-pyridinyl)benzamide (0.703 g, 1.86 mmol) N,N-dimethylformamide (1.9 mL) was added N-chlorosuccinimide (0.260 g, 1.95 mmol). The reaction mixture was stirred at 50° C. for 1 h. The temperature was raised to 70° C. for 1 h. The mixture was cooled to ambient temperature. Water was added. The mixture was extracted with diethyl ether (3×). The combined organic extracts were washed with water (3×), dried over magnesium sulfate, filtered and concentrated to give the title compound (0.795 g) MS 413.0 (M+1).

後処理

  1. temperatureThe temperature was raised to 70° C. for 1 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionThe mixture was extracted with diethyl ether (3×)
  4. washThe combined organic extracts were washed with water (3×)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fb9f2ac36cde4bbe95ec5fe6cafb0db8
出典データセット
uspto-grants-2013_06
特許番号
US08461185B2

反応ノート

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