7-{[2-(4-Morpholinyl)ethyl]amino}-6-nitro-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile → 6-Amino-7-{[2-(4-morpholinyl)ethyl]amino}-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile

HRID 989314Notes

Reaction equation

HRID 989314 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:30])[C:15]([C:28]#[N:29])=[CH:16][N:17]3[CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:12][C:11]=2[N+:31]([O-])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C1COCC1.C(O)C.[Pd]>[NH2:31][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:10]=1[NH:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[CH:16]=[C:15]([C:28]#[N:29])[C:14]2=[O:30]

Participants

5

Reactant 1

HCID 219564797-{[2-(4-Morpholinyl)ethyl]amino}-6-nitro-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile

Product 1

HCID 219563976-Amino-7-{[2-(4-morpholinyl)ethyl]amino}-4-oxo 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrileYield 110.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 916.4 mg (1.93 mmol) of 7-{[2-(4-morpholinyl)ethyl]amino}-6-nitro-4-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile in 52 mL of THF and 19 mL of ethanol is hydrogenated in a Parr apparatus at 40 psi for 6 hours in the presence of 183.3 mg of 10% palladium-on-carbon. The catalyst is removed by filtration and the solvent is evaporated in vacuo to give 944.0 mg of 6-amino-7-{[2-(4-morpholinyl)ethyl]amino}-4-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-3-quinolinecarbonitrile as a deep yellow solid which is used directly in the next step.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-98e3335c5eab4358afeef217eac5ea68
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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