Pyridine → HCID 178522850, compound

HRID 1808169Notes

Reaction equation

HRID 1808169 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C(Cl)Cl.[NH2:28][C:29]1[N:33]=[CH:32][NH:31][N:30]=1.N1C=CC=CC=1>>[NH:31]1[CH:32]=[N:33][C:29]([NH:28][S:17]([C:14]2[CH:15]=[CH:16][C:11]([C:9]([NH:8][CH2:7][C:6]3[CH:21]=[CH:22][C:3]([C:2]([F:24])([F:23])[F:1])=[CH:4][CH:5]=3)=[O:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[N:30]1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 57732025HCID 57732025, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178522850HCID 178522850, compoundYield 70.5%

Procedure

A solution/suspension of 4-(4-trifluoromethyl-benzylcarbamoyl)-benzenesulfonyl chloride (200 mg, 0.5 mmol) in methylene chloride (1.0 mL, 16 mmol) was added portion-wise to a 0° C. solution of 3-amino-1,2,4-triazole (48.9 mg, 0.581 mmol) in pyridine (1.0 mL, 12 mmol). After addition was complete, the ice-bath was removed, and the reaction mixture was warmed to rt. After 16 h, the reaction mixture was diluted with methylene chloride and partitioned with 1 N HCl. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, diluted with ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was loaded onto Celite and purified on the Isco (12 g cartridge, chloroform to 12% MeOH in chloroform) to afford the title compound (150 mg, 60%).

Workup

  1. additionAfter addition
  2. customthe ice-bath was removed
  3. additionthe reaction mixture was diluted with methylene chloride
  4. custompartitioned with 1 N HCl
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with methylene chloride
  7. washThe combined organic layers were washed with water
  8. additiondiluted with ethyl acetate
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. custompurified on the Isco (12 g cartridge, chloroform to 12% MeOH in chloroform)

Sources & evidence

ORD record
ord-239cba9cfb5848b5a40f93fbdc25da82
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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