HCID 59452626, compound → HCID 59452728, compound

HRID 419395Notes

Reaction equation

HRID 419395 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCOC(C)=O.CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]3[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH2:22][CH2:23]3)[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 1

HCID 59452626HCID 59452626, compound

Product 1

HCID 59452728HCID 59452728, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-[3-(methyloxy)-4-nitrophenyl]-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}piperazine (1.18 g, 2.76 mmol) in EtOAc (100 mL) and EtOH (25 mL) was added Pd on carbon in one portion. The mixture was stirred at rt under H2 (1 atm.) until complete by TLC. The reaction was filtered through Celite® and concentrated. Purification by flash chromatography provided the title compound of step F (0.690 g, 1.75 mmol, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31-1.42 (m, 2H), 1.75 (d, J=11.4 Hz, 2H), 1.86-1.97 (m, 2H), 2.15 (tt, J=11.3, 3.9 Hz, 1H), 2.54-2.59 (m, 4H), 2.65 (t, J=6.8 Hz, 2H), 2.88-2.94 (m, 6H), 3.00 (s, 3H), 3.25 (t, J=6.8 Hz, 2H), 3.71 (s, 3H), 4.18 (br. s., 2H), 6.25 (dd, J=8.4, 2.6 Hz, 1H), 6.46 (d, J=2.6 Hz, 1H), 6.49 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. concentrationconcentrated
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8f9520eb857c4566aa46a0235301c1a2
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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