Methane → HCID 53791749, compound

HRID 2232070Notes

Reaction equation

HRID 2232070 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]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=1.C(N(CC)CC)C.C>O1CCOCC1.C(Cl)Cl.C(O)CCC>[F:26][C:22]1[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]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 27613996-Fluoropyridin-2-amineHCID 199113037-chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride

Product 1

HCID 53791749HCID 53791749, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

7-Chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (12 g) is added, at a temperature between 60° and 70° C., to a solution of 2-amino-6-fluoropyridine (4.5 g) and triethylamine (8.1 g) in dioxane (250 cc) which is heated to a temperature in the vicinity of 60° C., in the course of 5 minutes. The suspension obtained is heated at a temperature in the vicinity of 100° C. for 6 hours and 45 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 (500 cc) and the solution obtained is washed twice with distilled water (300 cc in total), twice with an aqueous 2N sodium hydroxide solution (300 cc in total) and twice 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 (11.4 g) is thereby obtained, which is dissolved in boiling butan-1-ol (70 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 3 times with butan-1-ol (45 cc in total), twice with ethanol (50 cc in total) and 3 times with diethyl ether (90 cc in total) and then dried under the 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-(6-fluoro-2-pyridyl)-3-(3-pyridyl)-1H, 3H-pyrrolo[1,2- c]thiazole-7-carboxamide (5.3 g) in the form of beige-coloured crystals, m.p. 198° C., is thereby obtained.

Workup

  1. customThe suspension obtained
  2. temperatureis heated at a temperature in the vicinity of 100° C. for 6 hours and 45 minutes
  3. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  4. customThe residue obtained
  5. customthe solution obtained
  6. washis washed twice with distilled water (300 cc in total), twice with an aqueous 2N sodium hydroxide solution (300 cc in total) and twice with distilled water (300 cc in total)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. additiontreated with decolorizing charcoal (0.5 g)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50 ° C
  11. customA crude product (11.4 g) is thereby obtained
  12. dissolutionwhich is dissolved
  13. customobtained
  14. filtrationthe suspension is filtered in the heated state
  15. temperatureThe filtrate is cooled at a temperature in the vicinity of 4° C. for 2 hours
  16. customThe crystals formed
  17. customare separated by filtration
  18. washwashed 3 times with butan-1-ol (45 cc in total)
  19. dry with materialtwice with ethanol (50 cc in total) and 3 times with diethyl ether (90 cc in total) and then dried under the 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-90aa3fa65d774999b40903101103adde
Source dataset
uspto-grants-1988_11
Patent number
US04786645

Reaction notes

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