Pyridine → HCID 86746010, compound

HRID 654830Notes

Reaction equation

HRID 654830 reaction equation
C(N(C1C=CC([C:14]2[N:15]=[C:16]3[N:20]([CH:21]=2)[CH2:19][CH2:18][S:17]3)=CC=1)C(=O)C)CC.ClC(OCC)=O.C1C2C(CCCC2)CCC1.[S].[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[N:39]1[CH:44]=[CH:43][C:42]([C:21]2[N:20]3[C:16]([S:17][CH2:18][CH2:19]3)=[N:15][CH:14]=2)=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 1049Pyridine2×HCID 7044DecalinHCID 10928Ethyl chloroformate2×HCID 5362487SulfurHCID 19886437HCID 19886437, compound

Product 1

HCID 86746010HCID 86746010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The N-propylacetamido Formula (III) compound (0.60 g, 0.002 mole), prepared as described above in part a, was then suspended in CH2Cl2 (10 ml) and dry pyridine (0.47 ml, 0.006 mole) was added. The suspension was heated to aid in dissolving the solid, then cooled to ice-bath temperature. Ethyl chloroformate (0.72 ml, 0.648 g, 0.006 mole) in 2 ml CH2Cl2 was added dropwise to this mixture over a one hour period. The solution was stirred at room temperature for one hour and then heated at reflux for 10 min. The reaction was then cooled to 10° C. and an additional equivalent of pyridine (161 μl) and ethyl chloroformate (240 μl) was added. After heating at reflux for 10 min., the reaction was left to stir at room temperature overnight. The reaction was then washed with water (3×100 ml) and the organic layer stripped then decalin (5 ml) and sulfur (0.063 g, 0.002 mole) were added and the mixture was heated to 170° C. This temperature was maintained for one hour. The reaction was then diluted with CH2Cl2 and extracted with a 12% HCl solution. The acidic layer was basified with solid K2CO3 and then extracted with CH2Cl2. After treating with brine and MgSO4, the CH2Cl2 was removed, and the residue was flash chromatographed (0.10% MeOH/100-90% CH2Cl2) to give 0.2 g of a (Formula (I) compound), 6-4-(N-propylacetamido)phenyl)-5-(4-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole (TLC: Rf =0.22 5% MeOH/95% CH2Cl2.

Workup

  1. temperatureThe suspension was heated
  2. dissolutionin dissolving the solid
  3. temperaturecooled to ice-bath temperature
  4. temperatureheated
  5. temperatureat reflux for 10 min
  6. temperatureThe reaction was then cooled to 10° C.
  7. temperatureAfter heating
  8. temperatureat reflux for 10 min.
  9. waitthe reaction was left
  10. stirringto stir at room temperature overnight
  11. washThe reaction was then washed with water (3×100 ml)
  12. temperaturethe mixture was heated to 170° C
  13. temperatureThis temperature was maintained for one hour
  14. extractionextracted with a 12% HCl solution
  15. extractionextracted with CH2Cl2
  16. additionAfter treating with brine and MgSO4
  17. customthe CH2Cl2 was removed
  18. customchromatographed (0.10% MeOH/100-90% CH2Cl2)

Sources & evidence

ORD record
ord-b87008a206604c4292b661868822b88d
Source dataset
uspto-grants-1992_07
Patent number
US05134150

Reaction notes

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