Trifluoroacetic acid → HCID 52944034, compound

HRID 1510101Notes

Reaction equation

HRID 1510101 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[CH:22][CH:23]=3)[N:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:17]=2[O:40][C:41]2[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:42]=2[CH3:48])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:47][C:45]1[CH:44]=[CH:43][C:42]([CH3:48])=[C:41]([CH:46]=1)[O:40][C:17]1[N:18]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:19]2[C:24]([C:16]=1[C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:15])=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]([OH:29])=[O:28])[CH:20]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66920281HCID 66920281, compound

Product 1

HCID 52944034HCID 52944034, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of step 1 (88 mg, 133 μmol) was dissolved in DCM (20 ml), TFA (5 ml) was added, and the mixture was stirred at room temperature for 1 h. The solvents were evaporated and the obtained solid was purified by preparative HPLC. The eluate was lyophilized overnight. The residue was dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight. 45 mg of the title compound were obtained in the form of the [2-(5-fluoro-2-methyl-phenoxy)-1-phenyl-3-(piperazine-1-carbonyl)-1H-indol-6-yloxy]-acetic acid hydrochloride.

Workup

  1. customThe solvents were evaporated
  2. customthe obtained solid was purified by preparative HPLC
  3. waitThe eluate was lyophilized overnight
  4. dissolutionThe residue was dissolved in a small quantity of MOH
  5. additionmixed with hydrochloric acid (0.1 M)
  6. waitlyophilized overnight

Sources & evidence

ORD record
ord-e15ff86177c7401889481e07095bbb54
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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