HCID 66920449, compound → HCID 52949001, compound

HRID 1510095Notes

Reaction equation

HRID 1510095 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][CH2:27][O:28]CC4C=CC=CC=4)=[CH:22][CH:23]=3)[N:18]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]=2[CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([F:49])[C:44]=2[CH3:50])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)C.[Pd]>[F:49][C:45]1[C:44]([CH3:50])=[C:43]([CH:48]=[CH:47][CH:46]=1)[CH2:42][C:17]1[N:18]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:19]2[C:24]([C:16]=1[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15])=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][OH:28])[CH:20]=2

Participants

4

Reactant 1

HCID 66920449HCID 66920449, compound

Product 1

HCID 52949001HCID 52949001, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The compound of step 1 (20 mg, 30 μmol) was dissolved in ethanol (5 ml), palladium on carbon (4 mg) was added, and the mixture was stirred under an atmosphere of hydrogen at a pressure of 1.5 bar at room temperature for 3 h. The mixture was filtered over a pad of celite and evaporated under reduced pressure. The residue 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 dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight. 4 mg of the title compound were obtained in the form of the [2-(3-fluoro-2-methyl-benzyl)-6-(2-hydroxy-ethoxy)-1-phenyl-1H-indol-3-yl]-piperazin-1-yl-methanone hydrochloride.

Workup

  1. filtrationThe mixture was filtered over a pad of celite
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (20 ml)
  4. additionTFA (5 ml) was added
  5. stirringthe mixture was stirred at room temperature for 1 h
  6. customThe solvents were evaporated
  7. customthe obtained solid was purified by preparative HPLC
  8. waitThe eluate was lyophilized overnight
  9. dissolutionthe residue dissolved in a small quantity of MOH
  10. additionmixed with hydrochloric acid (0.1 M)
  11. waitlyophilized overnight

Sources & evidence

ORD record
ord-ecfe6e4a22784090bfe6644e47f24be8
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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