Hydrochloric Acid → HCID 22288819, compound

HRID 968296Notes

Reaction equation

HRID 968296 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].Cl[C:11]1[NH:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.Cl>C(O)C>[ClH:1].[NH:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[NH:4][C:3]1[C:5]([F:9])=[CH:6][CH:7]=[CH:8][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 785722-ChlorobenzimidazoleHCID 27342052-Chloro-6-fluoroaniline

Product 1

HCID 22288819HCID 22288819, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-fluoroaniline (0.48 g) and 2-chlorobenzimidazole (0.5 g) were mixed in a flask and then kept at 170° C. for 30 min. After cooling, the residue was dissolved out of the flask at boiling heat using 1 N HCl and 10% ethanol. The material dissolved out was then stirred at RT for 30 min, then the insoluble material was filtered off with suction and the filtrate was evaporated. The residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA). The clean fractions were combined, the acetonitrile was stripped off, the residue was adjusted to pH 10 with potassium carbonate solution, extracted three times with EA, and then the combined phases were dried, filtered, and concentrated. The residue was taken up using HCl/water and freeze-dried. 27 mg of the title compound were obtained.

Workup

  1. temperatureAfter cooling
  2. dissolutionthe residue was dissolved out of the flask
  3. temperatureat boiling heat
  4. dissolutionThe material dissolved out
  5. filtrationthe insoluble material was filtered off with suction
  6. customthe filtrate was evaporated
  7. customThe residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA)
  8. extractionextracted three times with EA
  9. customthe combined phases were dried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customfreeze-dried

Sources & evidence

ORD record
ord-0d06b77ea7b5430196bdb8ce8c7bbe7c
Source dataset
uspto-grants-2005_10
Patent number
US06958357B2

Reaction notes

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