Trifluoroacetic acid → HCID 136173806, compound

HRID 1161501Notes

Reaction equation

HRID 1161501 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[C:25](=[O:26])[NH:24][C:23]([CH:27]([C:41]2[CH:46]=[C:45]([CH2:47][CH3:48])[CH:44]=[C:43]([O:49][CH2:50][C:51](=[O:55])[N:52]([CH3:54])[CH3:53])[C:42]=2[F:56])[NH:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[N:39]=[C:38]([CH3:40])[O:37][N:36]=3)=[CH:31][CH:30]=2)=[N:22]1)(C)(C)C>ClCCl>[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[C:25](=[O:26])[NH:24][C:23]([CH:27]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[N:39]=[C:38]([CH3:40])[O:37][N:36]=3)=[CH:33][CH:34]=2)[C:41]2[C:42]([F:56])=[C:43]([CH:44]=[C:45]([CH2:47][CH3:48])[CH:46]=2)[O:49][CH2:50][C:51]([N:52]([CH3:54])[CH3:53])=[O:55])=[N:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136173745HCID 136173745, compound

Product 1

HCID 136173806HCID 136173806, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 2 ml of trifluoroacetic acid to a solution of 0.135 g of [2-(3-{(3-dimethylcarbamoylmethoxy-5-ethyl-2-fluorophenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-1-yl)phenyl]carbamic acid t-butyl ester in 10 ml of dichloromethane, the reaction mixture was stirred at room temperature for 4 hours, and the solvent was removed under reduced pressure. Next, 50 ml of ethyl acetate and 5 ml of 5% aqueous potassium carbonate were added to the residue, and the organic layer was washed with 20 ml of water and 20 ml of saturated aqueous sodium chloride in that order. The aqueous layer was extracted with 50 ml of ethyl acetate, and then the organic layers were combined and dried over anhydrous magnesium sulfate, the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The title compound (0.100 g) was obtained as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionNext, 50 ml of ethyl acetate and 5 ml of 5% aqueous potassium carbonate were added to the residue
  3. washthe organic layer was washed with 20 ml of water and 20 ml of saturated aqueous sodium chloride in that order
  4. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationthe desiccating agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bfbc62c5af9d475ca4fc2fc37851dcac
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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