HCID 59441658, compound → HCID 59441971, compound

HRID 1014328Notes

Reaction equation

HRID 1014328 reaction equation
[CH3:1][C@H:2]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>C(O)C.[Pd]>[CH2:23]([N:19]([CH2:20][CH2:21][CH3:22])[C@@H:2]([CH3:1])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([NH2:14])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4])[CH2:24][CH3:25]

Participants

4

Reactant 1

HCID 59441658HCID 59441658, compound

Product 1

HCID 59441971HCID 59441971, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-{(1S)-1-methyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-N-propyl-1-propanamine (0.6 g, 1.72 mmols) in absolute ethanol (50 mL) was maintained under 45 psi H2(g) with catalytic 10% Pd/C for 16 hours. The catalyst was removed by vacuum filtration through a celite pad and rinsed with methanol. The filtrate was collected, concentrated under reduced pressure, and dried under high vacuum to give 1-[(2S)-2-(dipropylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine. ESIMS (M+H)+=320.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-ad9ff24259694de499d7de949288a3b6
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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