Pyridine → 2,6-difluoro-N-[4-[(Z)-hydroxyiminomethyl]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamide

HRID 1255135Notes

Reaction equation

HRID 1255135 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH:12]=O)[N:11]=1)=[O:5].Cl.[NH2:30][OH:31].N1C=CC=CC=1>CCO.C(Cl)Cl>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10](/[CH:12]=[N:30]\[OH:31])[N:11]=1)=[O:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 24765490HCID 24765490, compound

Product 1

HCID 590045602,6-difluoro-N-[4-[(Z)-hydroxyiminomethyl]-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzamideYield 52.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Into a solution of Compound 67 (180 mg, 0.44 mmol) in 3 mL of EtOH was added hydroxylamine hydrochloride (60 mg, 0.9 mmol) and pyridine (0.5 mL). The solution was stirred at room temperature for 2 hours. The reaction was diluted with 20 mL of CH2Cl2, and the solution was washed with 10 mL of water and dried (Na2SO4), filtered and concentrated. The residue was purified on silica (eluted with 5-100% ethyl acetate in hexane) to give Compound 72 (98 mg, 52%) as a white solid.

Workup

  1. washthe solution was washed with 10 mL of water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica (eluted with 5-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3a166eeedc144869abfcb07c838c2f52
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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