Toluene → HCID 22032300, compound

HRID 1792464Notes

Reaction equation

HRID 1792464 reaction equation
C1(C(Cl)=O)CC1.[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([C:17]([NH:19][NH2:20])=O)=[CH:15][N:16]=2)[CH:13]=1.C(=O)(O)[O-].[Na+].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1.[C:48]1([CH3:54])[CH:53]=[CH:52]C=CC=1>O.O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([C:17]3[S:35][C:54]([CH:48]4[CH2:53][CH2:52]4)=[N:20][N:19]=3)=[CH:15][N:16]=2)[CH:13]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 77637Cyclopropanecarbonyl chlorideHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 23537414HCID 23537414, compound

Product 1

HCID 22032300HCID 22032300, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.22 mL cyclopropane carbonyl chloride was added at room temperature to a mixture of 510 mg 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid hydrazide (compound in Production Example 276), 202 mg sodium bicarbonate, 15 mL tetrahydrofuran and 15 mL water, and the mixture was stirred overnight. The organic layer was separated by adding saturated sodium bicarbonate, common salt and tetrahydrofuran to the reaction solution. The aqueous layer was further extracted with tetrahydrofuran, and the combined organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. Diisopropyl ether was added to the resulting residues, and the formed crystals were collected by filtration and dried under reduced pressure by a vacuum pump. 606 mg crude product of cyclopropane carboxylic acid N′-(6-bromoimidazo[1,2-a]-pyridine-3-carbonyl)hydrazide was obtained as pale brown crystals. A mixture of 200 mg of this carboxylic acid hydrazide derivative, 250 mg Lawesson's reagent and 20 mL anhydrous toluene was heated for 1 hour under reflux. The reaction solution was evaporated, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 48 mg of the title compound as a white solid.

Workup

  1. customThe organic layer was separated
  2. additionby adding saturated sodium bicarbonate, common salt and tetrahydrofuran to the reaction solution
  3. extractionThe aqueous layer was further extracted with tetrahydrofuran
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. customthe filtrate was evaporated
  8. additionDiisopropyl ether was added to the resulting residues
  9. filtrationthe formed crystals were collected by filtration
  10. customdried under reduced pressure by a vacuum pump
  11. custom606 mg crude product of cyclopropane carboxylic acid N′-(6-bromoimidazo[1,2-a]-pyridine-3-carbonyl)hydrazide was obtained as pale brown crystals
  12. temperaturewas heated for 1 hour
  13. temperatureunder reflux
  14. customThe reaction solution was evaporated
  15. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6daa03a51b114bf9858fad4788a0195e
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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