HCID 178470425, compound → HCID 178518629, compound

HRID 428437Notes

Reaction equation

HRID 428437 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[C:9]([C:18]([F:21])([F:20])[F:19])=[N:10][NH:11][C:12]=2[C:13]([O:15]CC)=O)=[O:7])=[C:4]([NH2:24])[CH:3]=1.OC1C=CC=CN=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6](=[O:7])[C:8]3[C:9]([C:18]([F:19])([F:20])[F:21])=[N:10][NH:11][C:12]=3[C:13](=[O:15])[NH:24][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 178470425HCID 178470425, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 178518629HCID 178518629, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of ethyl 4-(4-chloro-2-aminobenzoyl)-3-trifluoromethyl-1H-pyrazole-5-carboxylate (360 mg, 0.997 mmol) in toluene (50 mL) was added 2-hydroxypyridine (93.9 mg, 0.988 mmol). Toluene was removed by distillation and the residue was heated at 170° C. for 2 days. The flask was cooled to room temperature and dichloromethane (20 mL) was added. The insoluble material was filtered to give crude solid (284 mg). The crude material was continuously chromatographed eluting with dichloromethane (100 mL) and dichloromethane:2-propanol (98:2, 200 mL). The fractions were concentrated by rotary evaporation and were found to contain a contaminant from tygon tubing. The fractions were combined and flash chromatographed through a plug of silica gel to remove the contaminant, eluting with hexanes, hexanes:ethyl acetate (95:5, 90:10), dichloromethane, and dichloromethane:2-propanol (95:5, 90:10). The product fractions were concentrated by rotary evaporation to give the title compound as a white solid (124 mg, 37%, m.p. 337-339° C.).

Workup

  1. customToluene was removed by distillation
  2. temperatureThe flask was cooled to room temperature
  3. additiondichloromethane (20 mL) was added
  4. filtrationThe insoluble material was filtered
  5. customto give crude solid (284 mg)
  6. customThe crude material was continuously chromatographed
  7. washeluting with dichloromethane (100 mL) and dichloromethane:2-propanol (98:2, 200 mL)
  8. concentrationThe fractions were concentrated by rotary evaporation
  9. customflash chromatographed through a plug of silica gel
  10. customto remove the contaminant
  11. washeluting with hexanes, hexanes:ethyl acetate (95:5, 90:10), dichloromethane, and dichloromethane:2-propanol (95:5, 90:10)
  12. concentrationThe product fractions were concentrated by rotary evaporation

Sources & evidence

ORD record
ord-16e231c600fd4146accce8d4d51ae4ac
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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