Methane → N-(3-benzoylphenyl)-3-pyridin-3-yl-1,3-dihydropyrrolo[1,2-c][1,3]thiazole-7-carboxamide

HRID 2231735Notes

Reaction equation

HRID 2231735 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:16]([OH:18])=O)=[C:11]3[CH2:10][S:9]2)[CH:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].C>O1CCOCC1.C(O)C.O.C(N(CC)CC)C>[C:23]([C:22]1[CH:21]=[C:20]([NH:19][C:16]([C:15]2[CH:14]=[CH:13][N:12]3[C:11]=2[CH2:10][S:9][CH:8]3[C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)=[O:18])[CH:33]=[CH:32][CH:31]=1)(=[O:24])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 17817Methanone, (3-aminophenyl)phenyl-HCID 13339277(+)-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid

Product 1

HCID 65927N-(3-benzoylphenyl)-3-pyridin-3-yl-1,3-dihydropyrrolo[1,2-c][1,3]thiazole-7-carboxamide

Reagents, catalysts & solvents 3

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrochloride of the acid chloride derived from (+)-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid (24.5 g) is added, at a temperature between 60° and 72° C., to a solution of 3-aminobenzophenone (16.1 g) and triethylamine (16.5 g) in dioxane (420 cc) which is heated to a temperature in the vicinity of 60° C., in the course of 5 minutes. The suspension obtained is heated, with stirring, at a temperature in the vicinity of 100° C. for 6 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 is dissolved in ethyl acetate (750 cc). The solution obtained is washed 3 times with distilled water (800 cc in total), twice with a saturated aqueous sodium bicarbonate solution (600cc in total) and twice with distilled water (600 cc in total) and then dried over anhydrous magnesium sulphate, treated with decolourizing 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 60° C. Crude product (36 g) is thereby obtained, which is dissolved in a boiling ethanol:water (85:15 by volume) mixture (200 cc). Decolourizing 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 20° C. for 3 hours. The crystals formed are separated by filtration, washed 3 times with an ethanol: water (85:15 by volume) mixture (75 cc in total) and 4 times with diethylether (200 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-(3-benzoylphenyl)-3-(3-pyridyl)-1H,2H-pyrrolo[1,2-c]thiazole-7-carboxamide in the hydrated state (20.7 g), in the form of cream-coloured crystals, m.p. 109° 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. dissolutionThe residue is dissolved in ethyl acetate (750 cc)
  6. customThe solution obtained
  7. washis washed 3 times with distilled water (800 cc in total)
  8. dry with materialtwice with a saturated aqueous sodium bicarbonate solution (600cc in total) and twice with distilled water (600 cc in total) and then dried over anhydrous magnesium sulphate
  9. additiontreated with decolourizing 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 60° C
  12. customCrude product (36 g) is thereby obtained
  13. customobtained
  14. filtrationthe suspension is filtered in the heated state
  15. temperatureThe filtrate is cooled at a temperature in the vicinity of 20° C. for 3 hours
  16. customThe crystals formed
  17. customare separated by filtration
  18. washwashed 3 times with an ethanol: water (85:15 by volume) mixture (75 cc in total) and 4 times with diethylether (200 cc in total)
  19. 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-14523798318a4a5690c414b440ead441
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Reaction notes

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