Pyridine → HCID 67715516, compound

HRID 1449520Notes

Reaction equation

HRID 1449520 reaction equation
N1C=CC=C[CH:2]=1.Cl.[CH2:8]([C:11]1[N:15]2[CH2:16][CH2:17][CH2:18][N:19]=[C:14]2[S:13][C:12]=1[C:20]([Cl:22])=[O:21])[CH2:9][CH3:10].[CH2:23]([NH2:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]C.CNC1C=NC=C(NC)C=1>CN(C)C=O>[ClH:22].[CH2:32]([CH:31]([CH3:2])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]/[CH:24]=[CH:23]\[NH:41][C:20]([C:12]1[S:13][C:14]2=[N:19][CH2:18][CH2:17][CH2:16][N:15]2[C:11]=1[CH2:8][CH2:9][CH3:10])=[O:21])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5356789OleylamineHCID 19978122HCID 19978122, compoundHCID 54501726HCID 54501726, compound

Product 1

HCID 67715516HCID 67715516, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In the mixture of 30 ml of pyridine and 3 ml of dimethylformamide was suspended 849 mg of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride (described in Example 13). To the suspension were added 807 mg of oleyl amine and 36 mg of 3,5-dimethylaminopyridine, followed by stirring at 70° C. for 20 hours. The reaction mixture was concentrated and to the concentrate was added saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and treated with active carbon. The solvent was removed under reduced pressure. The residue was dissolved in ethanol and to the solution was added saturated hydrogenchloride diethylether solution, followed by stirring at room temperature. After removing the solvent, the residue was purified by silica gel column chromatography (silica gel: 150 g) using a mixed solvent of chloroform and methanol (20:1 by volume). The purified substance was added to saturated hydrogenchloride diethylether solution, followed by stirring at room temperature. The solvent was removed under reduced pressure. The residue was crystallized from hexane-diethylether to obtain 203 mg of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated and to the concentrate
  2. additionwas added saturated sodium hydrogencarbonate aqueous solution
  3. extractionThe mixture was extracted with chloroform
  4. washThe extract was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. additiontreated with active carbon
  7. customThe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in ethanol and to the solution
  9. additionwas added saturated hydrogenchloride diethylether solution
  10. stirringby stirring at room temperature
  11. customAfter removing the solvent
  12. customthe residue was purified by silica gel column chromatography (silica gel: 150 g)
  13. additionThe purified substance was added to saturated hydrogenchloride diethylether solution
  14. stirringby stirring at room temperature
  15. customThe solvent was removed under reduced pressure
  16. customThe residue was crystallized from hexane-diethylether

Sources & evidence

ORD record
ord-889c71bf46ad4d048d420a652fecba55
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

Loading…