4-Aminopyridine → HCID 19683070, compound

HRID 2250832Notes

Reaction equation

HRID 2250832 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:15]([S:19](Cl)(=[O:21])=[O:20])[CH2:16][CH2:17][CH3:18]>C1COCC1.C(Cl)Cl>[CH2:15]([S:19]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)(=[O:21])=[O:20])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 754301-Butanesulfonyl chloride

Product 1

HCID 19683070HCID 19683070, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

51.0 g of 4-aminopyridine (0.542 mol) and 75.0 ml of triethylamine (54.8 g, 0.542 mol) were dissolved at 50° C. in 540 ml of THF. Again at 50° C., 70.3 ml of n-butanesulphonyl chloride (84.9 g, 0.542 mol) were added dropwise to this solution over the course of 1 h. After 19 h of stirring at 50° C. the reaction mixture was diluted with 500 ml of methylene chloride and extracted twice with 500 ml of 1 N NaOH. The aqueous phase was adjusted to a pH of 6-7 with concentrated HCl and then extracted with 500 ml of methylene chloride. The organic phase was dried over magnesium sulphate and the methylene chloride was removed by distillation. The 30 g of crude product obtained were recrystallized from acetonitrile. This gave 19.0 g of clean product. The constitution of the compound was verified by NMR-spectroscopy.

Workup

  1. extractionextracted twice with 500 ml of 1 N NaOH
  2. extractionextracted with 500 ml of methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customthe methylene chloride was removed by distillation

Sources & evidence

ORD record
ord-7d0476fc8d964790bcde55ae0bde3bfc
Source dataset
uspto-grants-2008_01
Patent number
US07317112B2

Reaction notes

Loading…