HCID 58011753, compound → HCID 58012293, compound

HRID 660960Notes

Reaction equation

HRID 660960 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][C:25]([CH3:37])([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[CH3:26])=[O:23])[N:9]=2)=[CH:4][CH:3]=1>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][C:25]([CH3:37])([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=3)[CH3:26])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58011753HCID 58011753, compound

Product 1

HCID 58012293HCID 58012293, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.2 g (2.18 mmol) of 2-[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 452 are dissolved in 30 ml of dichloromethane and treated at 0° C. with 1.2 g (2.83 mmol) of 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane). This is stirred for 3 hrs at RT. The reaction solution is then diluted with 30 ml of ethyl acetate and washed three times with 15 ml of 1 N aqueous sodium hydroxide each time. The organic phase is dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate first 4:1, then 1:1). 0.90 g (75% of theory) of the target compound are obtained.

Workup

  1. washwashed three times with 15 ml of 1 N aqueous sodium hydroxide each time
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography on silica gel (eluent
  6. custom0.90 g (75% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-480b2ee8db2f443da9c17c606c4aa692
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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