HCID 11142629, compound → HCID 10923241, compound

HRID 392771Notes

Reaction equation

HRID 392771 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])=[CH:12]2)C1C=CC=CC=1>C(O)C.C(OC(=O)C)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])=[CH:12]2

Participants

5

Reactant 1

HCID 11142629HCID 11142629, compound

Product 1

HCID 10923241HCID 10923241, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Example 5, (5-Benzyloxy-1H-indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (0.2 g) in a mixture of ethanol (3 mL) and ethylacetate (5 mL) was treated with 10% palladium on carbon (approximately 0.025 g) and hydrogenated at atmospheric pressure for 2 h. The reaction mixture was filtered through a pad of Celite and the residue washed with methanol. The solvent in the combined filtrates was removed under reduced pressure, and the residue was purified via silica gel chromatography (3-10% 2 M ammonia in methanol/dichloromethane) to afford the title compound (0.034 g, 23%). 1H NMR (400 MHz, CD3OD): δ 7.20 (d, J=8.0 Hz, 1H), 6.90 (m, 1H), 6.75 (dd, J=4, 8 Hz, 1H), 6.54 (m,1H), 3.80 (br.m, 4H), 2.44 (m, 4H), 2.27 (s, 3H). MS (electrospray): exact mass calculated for C14H17N3O2, 259.13; m/z found, 260.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe residue washed with methanol
  3. customThe solvent in the combined filtrates was removed under reduced pressure
  4. customthe residue was purified via silica gel chromatography (3-10% 2 M ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-f2de1cec1de1479ab980f6e84150b785
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

Loading…