Ethanol → 4-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid

HRID 2190601Notes

Reaction equation

HRID 2190601 reaction equation
C([O:8][C:9](=[O:42])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:41])[NH:29][C:30]4[CH:38]=[C:37]5[C:33]([CH:34]=[CH:35][N:36]5[CH2:39][CH3:40])=[CH:32][CH:31]=4)=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.CCO.[H][H]>[Pd].CCOC(C)=O>[CH2:39]([N:36]1[C:37]2[C:33](=[CH:32][CH:31]=[C:30]([NH:29][C:28]([C:25]3[CH:26]=[CH:27][C:22]([N:19]4[CH2:18][CH2:17][N:16]([C:13]5[CH:12]=[CH:11][C:10]([C:9]([OH:42])=[O:8])=[CH:15][CH:14]=5)[CH2:21][CH2:20]4)=[N:23][CH:24]=3)=[O:41])[CH:38]=2)[CH:34]=[CH:35]1)[CH3:40]

Participants

6

Reactant 3

HCID 702EthanolHCID 593181154-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 462029724-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-{4-[5-(1-ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid benzyl ester (100 mg, 0.18 mmol), 10% Pd/C (50 mg) in a 1:1 mixture of EtOH and EtOAc (50 mL) was hydrogenated under 1 atm of hydrogen for 2 h. The mixture was then filtered. The solids were washed with a 1:1 mixture of THF and DMF and the combined organic layer was concentrated. The residue was passed through a silica gel plug with DMF to afford the product (85 mg; Yield: 96%). HRMS m/z calcd for C27H27N5O3I [M+H]+: 470.2187. Found: 470.2184.

Workup

  1. filtrationThe mixture was then filtered
  2. washThe solids were washed with a 1:1 mixture of THF and DMF
  3. concentrationthe combined organic layer was concentrated
  4. customto afford the product (85 mg; Yield: 96%)

Sources & evidence

ORD record
ord-341e9c5ba2d249e0a81f4ec9e28e5387
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

Loading…