Piperazine → 6-(Piperazin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide

HRID 1670589ノート

反応式

HRID 1670589 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CN(C=O)C>[N:17]1([C:2]2[N:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

参加物

4

反応物 2

HCID 4837PiperazineHCID 9431916-chloro-N-(1,3-thiazol-2-yl)pyridine-3-sulfonamide

生成物 1

HCID 576658046-(Piperazin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide収率 17.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-chloro-N-(thiazol-2-yl)pyridine-3-sulfonamide (8.2 g, 30 mmol) and piperazine (12.5 g, 145 mmol) in DMF (150 mL) was heated to 80° C. overnight under a nitrogen atmosphere. The reaction mixture was evaporated to dryness under reduced pressure and purified by column chromatography over silica gel with dichloromethane/20% 3.5 M NH3 in methanol. The product containing fractions were dissolved in a minimal amount of water and methanol and purified by reversed phase column chromatography (ISCO) with a gradient of water and methanol. After about half of the solution was purified, crystals had formed in the liquid. This material was collected by filtration washed with methanol to yield additional material. In total 1.7 g (17%) of 6-(Piperazin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide was obtained. 1H-NMR (300 MHz, DMSO-d6): δ 8.41 (d, J=2.3 Hz, 1H), 7.76 (dd, J=2.3, 9.0 Hz, 1H), 7.02 (d, J=4.1 Hz, 1H), 6.82 (d, J=9.0 Hz, 1H), 6.55 (d, J=4.1 Hz, 1H), 3.62-3.58 (m, 4H), 2.94-2.90 (m, 4H) ppm.

後処理

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. custompurified by column chromatography over silica gel with dichloromethane/20% 3.5 M NH3 in methanol
  3. additionThe product containing fractions
  4. dissolutionwere dissolved in a minimal amount of water and methanol
  5. custompurified by reversed phase column chromatography (ISCO) with a gradient of water and methanol
  6. customAfter about half of the solution was purified
  7. customcrystals had formed in the liquid
  8. filtrationThis material was collected by filtration
  9. washwashed with methanol
  10. customto yield additional material

出典と根拠

ORDレコード
ord-a9183c65e49645f0a23af115d7ab5e12
出典データセット
uspto-grants-2011_08
特許番号
US07994174B2

反応ノート

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