Trifluoroacetic acid → HCID 178442319, compound

HRID 396142Notes

Reaction equation

HRID 396142 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:31][C:32](=[O:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:5]=[C:6]([CH3:30])[C:7]=1[O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](C(OC(C)(C)C)=O)[N:13]=[C:12]2[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:36]([O:35][C:33](=[O:34])[C:32]([NH:31][C:4]1[CH:5]=[C:6]([CH3:30])[C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[C:12]3[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:2]([CH3:1])[CH:3]=1)=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21353741HCID 21353741, compound

Product 1

HCID 178442319HCID 178442319, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 474 mg (0.905 mmol) of ethyl ({3,5-dimethyl-4-[(1-tert-butoxycarbonyl-3-pentylindazol-5-yl)oxy]phenyl]}amino)(oxo) acetate (Example 13) and 2.58 g (22.63 mmol) of trifluoroacetic acid in 30 ml of methylene chloride is stirred at room temperature overnight. The mixture is subsequently concentrated in vacuo and the residue obtained is purified on silica gel using cyclohexane/ethyl acetate 3:2. 391 mg (99% of theory) of ethyl-({3,5-dimethyl-4-[(3-pentyl-1H-indazol-5-yl)oxy]phenyl}amino)(oxo)acetate are obtained.

Workup

  1. concentrationThe mixture is subsequently concentrated in vacuo
  2. customthe residue obtained
  3. customis purified on silica gel

Sources & evidence

ORD record
ord-938ebc2ffc3644f483db037b597dcf9d
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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