HCID 18467100, compound → HCID 18467087, compound

HRID 2229403Notes

Reaction equation

HRID 2229403 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([NH:36]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:29][C:28]=2[CH:56]([CH3:58])[CH3:57])=[O:25])[C:6]1=[O:59])[CH2:2][CH2:3][CH3:4]>C(O)C.[C].[Pd]>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([NH2:36])=[CH:29][C:28]=2[CH:56]([CH3:58])[CH3:57])=[O:25])[C:6]1=[O:59])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 18467100HCID 18467100, compound

Product 1

HCID 18467087HCID 18467087, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A suspension of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-(2,6-diisopropyl-4-tritylaminophenyl)urea (273 mg, 0.348 mmol), a 10% palladium carbon (56 mg) in ethanol is stirred under hydrogen atmosphere at room temperature for 8 hours. The mixture is filtered on celite, and the solvent is concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give the title compound (165 mg, 0.30 mmol) as crystals.

Workup

  1. filtrationThe mixture is filtered on celite
  2. concentrationthe solvent is concentrated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-731209998c7b4640ba1d6cdcfd32e4b1
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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