Pyridine → HCID 54427903, compound

HRID 567710Notes

Reaction equation

HRID 567710 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[C:8]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]=2[NH:10][N:11]=1)=[O:5])[CH3:2].N1C=CC=CC=1.C1(C)C=CC(S([Cl:33])(=O)=O)=CC=1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[N:10][C:9]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:8]=2[C:7]=1[Cl:33])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 54199326HCID 54199326, compound

Product 1

HCID 54427903HCID 54427903, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-oxo-4,5,6,7,8,9-hexahydro-1H-cyclohepta[c]pyridazine-3-carboxylic acid ethyl ester (2.7 g) and pyridine (0.93 ml) in dichloromethane (150 ml) was added p-toluenesulphonyl chloride (2.2 g). The reaction mixture was heated at reflux for 20 h. The reaction mixture was washed with 1M potassium carbonate solution, brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was purified by flash chromatography using a gradient elution: CH2Cl2 (500 ml), CH2Cl2/MeOH 99:1 (500 ml), CH2Cl2/MeOH 98:2 (500 ml), CH2Cl2/MeOH 97:3 (500 ml), CH2Cl2/MeOH 96:4 (500 ml). The appropriate fractions were combined and evaporated under reduced pressure to give a solid (0.65 g, 22%). C12H15ClN2O2 requires C, 56.58; H, 5.93; N, 11.00. Found C, 56.52; H, 6.06; N, 11.01%. δH (360 MHz; CDCl3) 1.44 (3H, t, J=7 Hz, CH3), 1.70 (2H, m, CH2), 1.77 (2H, m, CH2), 1.92 (2H, m, CH2), 3.06 (2H, m, CH2), 3.32 (2H, m, CH2), 4.51 (2H, t, J=7 Hz, CH2), m/z (ESP+) 255/257 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. washThe reaction mixture was washed with 1M potassium carbonate solution, brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe oil was purified by flash chromatography
  9. washa gradient elution
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-17976bdf4ef043ee8a3cc34941b78e29
Source dataset
uspto-grants-2001_01
Patent number
US06180630B2

Reaction notes

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