4-Fluorobenzenesulfonyl chloride → N-(3,5-dimethylpyridin-2-yl)-4-fluorobenzenesulfonamide

HRID 594103

反応式

HRID 594103 の反応式
[CH3:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:1][C:2]1[C:3]([NH:9][S:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

参加物

4

反応物 2

HCID 95884-Fluorobenzenesulfonyl chloride2 回HCID 30163103,5-Dimethylpyridin-2-amine

生成物 1

HCID 89876077N-(3,5-dimethylpyridin-2-yl)-4-fluorobenzenesulfonamide収率 28.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
20 °C

実験手順

To a stirred solution of 3,5-dimethylpyridin-2-amine (129 mg, 1.056 mmol) in pyridine (5 mL) at room temperature, was added 4-fluorobenzene-1-sulfonyl chloride (205 mg, 1.056 mmol). The reaction mixture was stirred at 20° C. for 30 minutes, then left to stand for 16 hours. Additional 4-fluorobenzene-1-sulfonyl chloride (205 mg, 1.056 mmol) was then added and the reaction stirred for an additional 4 hours. The reaction mixture was concentrated in vacuo and purified by passing through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol, followed by a sulphonic acid (SCX) SPE cartridge eluting with methanol then 2M ammonia/methanol. Concentration of the product-containing fractions provided the title compound (84.1 mg) as a yellow oil. LCMS (2 min, formic) Rt 0.89 min, m/z (ES+) 281 (M+H).

後処理

  1. waitleft
  2. waitto stand for 16 hours
  3. stirringthe reaction stirred for an additional 4 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompurified
  6. extractionby passing through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
  7. washeluting with methanol
  8. washeluting with methanol

出典と根拠

ORDレコード
ord-413c661d6cc94633b6f614c4ceb3ac46
出典データセット
uspto-grants-2016_01
特許番号
US09242972B2

関連ノート

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