Methane → HCID 21284364, compound

HRID 2232072Notes

Reaction equation

HRID 2232072 reaction equation
Cl.Cl[C:3]([C:5]1[CH:6]=[CH:7][N:8]2[C:12]=1[CH2:11][S:10][CH:9]2[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:4].[NH2:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][N:21]=1.C(N(CC)CC)C.C>O1CCOCC1.C(Cl)Cl.C(#N)C>[Cl:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([NH:19][C:3]([C:5]2[CH:6]=[CH:7][N:8]3[C:12]=2[CH2:11][S:10][CH:9]3[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:4])[CH:25]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 5818662-Amino-4-chloropyridineHCID 199113037-chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride

Product 1

HCID 21284364HCID 21284364, compoundYield 36.6%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
67 °C

Procedure

7-Chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (6 g) is added, at a temperature in the vicinity of 67° C., to a solution of 2-amino-4-chloropyridine (2.6 g) and triethylamine (4.05 g) in dioxane (150 cc) which is heated to a temperature in the vicinity of 67° C., in the course of 15 minutes. The suspension obtained is heated, with stirring, at a temperature in the vicinity of 100° C. for 7 hours and 30 minutes and then stirred at a temperature in the vicinity of 20° C. for 16 hours. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. The residue obtained is dissolved in methylene chloride (350 cc). The solution obtained is washed twice with distilled water (200 cc in total), twice with an aqueous 1N sodium hydroxide solution (200 cc in total) and 3 times with distilled water (300 cc in total) and then dried over anhydrous magnesium sulphate, treated with decolorizing charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C. A crude product (5 g) is thereby obtained, which is dissolved in boiling acetonitrile (200 cc). Decolorizing charcoal (0.5 g) is added to the solution obtained and the suspension is filtered in the heated state. The filtrate is cooled at a temperature in the vicinity of 4° C. for 2 hours. The crystals formed are separated by filtration, washed twice with acetonitrile cooled to a temperature in the vicinity of 4° C. (10 cc in total) and twice with diethyl ether (20 cc in total) and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets. N-(4-chloro-2-pyridyl)-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (2.6 g) in the form of cream-coloured cyrstals, m.p. 190° C., is thereby obtained.

Workup

  1. customThe suspension obtained
  2. temperatureis heated
  3. stirringstirred at a temperature in the vicinity of 20° C. for 16 hours
  4. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  5. customThe residue obtained
  6. customThe solution obtained
  7. washis washed twice with distilled water (200 cc in total), twice with an aqueous 1N sodium hydroxide solution (200 cc in total) and 3 times with distilled water (300 cc in total)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. additiontreated with decolorizing charcoal (0.5 g)
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C
  12. customA crude product (5 g) is thereby obtained
  13. dissolutionwhich is dissolved
  14. customobtained
  15. filtrationthe suspension is filtered in the heated state
  16. temperatureThe filtrate is cooled at a temperature in the vicinity of 4° C. for 2 hours
  17. customThe crystals formed
  18. customare separated by filtration
  19. washwashed twice with acetonitrile
  20. temperaturecooled to a temperature in the vicinity of 4° C. (10 cc in total) and twice with diethyl ether (20 cc in total)
  21. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-6f3d262c98494a26b272d65da5d9c454
Source dataset
uspto-grants-1988_11
Patent number
US04786645

Reaction notes

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