HCID 22181339, compound → HCID 22181380, compound

HRID 1796464Notes

Reaction equation

HRID 1796464 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH:4]([NH:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:12])=[CH:9][C:8]=1[N+:20]([O-])=O)[CH3:5]>CCOC(C)=O.[Pd]>[NH2:20][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][C:7]=1[NH:6][CH:4]([CH3:5])[CH2:3][N:2]([CH3:1])[CH3:23])[C:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 22181339HCID 22181339, compound

Product 1

HCID 22181380HCID 22181380, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 2C: A mixture of 4-{[2-(dimethylamino)-1-methylethyl]amino}-N,N-diethyl-3-nitrobenzamide (0.516 g, 1.60 mmol) and 10% Pd/C in EtOAc (20 mL) was hydrogenated overnight at 35 psi. Usual work-up provided the title compound (0.408 g, 87%) which was used without further purification. 1H-NMR (CDCl3): δ 6.82 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 6.77 (d, J=2.4 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 3.52–336 (m, 6H), 2.52 (dd, J=12.0 Hz, J=9.6 Hz, 2H), 2.28–2.19 (m, 7H), 1.17 (m, 8H). MS (ESI) (M+H)+=293.

Sources & evidence

ORD record
ord-b23cf25d791a4e8f8b7b7577508bb7ab
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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