HCID 68793200, compound → HCID 68791600, compound

HRID 1784319Notes

Reaction equation

HRID 1784319 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[C:9]([C:16]([CH3:29])([CH3:28])[C:17]([N:19]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:13][C:12]1[CH:11]=[CH:10][C:9]([C:16]([CH3:29])([CH3:28])[C:17]([N:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:18])=[CH:8][C:7]=1[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:30])[CH3:1]

Participants

4

Reactant 1

HCID 68793200HCID 68793200, compound

Product 1

HCID 68791600HCID 68791600, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Conditions

Temperature
20 °C

Procedure

2-(3-{[3-(dimethylamino)propyl]amino}-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (44 mg) in solution in a mixture of ethyl acetate/ethanol 2:1 (3 ml), and 10% palladium on carbon (5 mg) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C., the catalyst is eliminated by filtration on celite and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (39 mg; 95% yield).

Workup

  1. additionare introduced into an autoclave
  2. filtrationthe catalyst is eliminated by filtration on celite
  3. concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-9261c4e1f3794937949ea4a425d4a58d
Source dataset
uspto-grants-2009_03
Patent number
US07501525B2

Reaction notes

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