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

HRID 1670589Notes

Reaction equation

HRID 1670589 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a9183c65e49645f0a23af115d7ab5e12
Source dataset
uspto-grants-2011_08
Patent number
US07994174B2

Reaction notes

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