HCID 22106143, compound → HCID 67552825, compound

HRID 1456401Notes

Reaction equation

HRID 1456401 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][CH2:22][C:23]#[C:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH:16]=2)=[C:7]([NH:31][C:32]([NH:34][C:35]2[C:40]([CH:41]([CH3:43])[CH3:42])=[CH:39][CH:38]=[CH:37][C:36]=2[CH:44]([CH3:46])[CH3:45])=[O:33])[C:6]1=[O:47])[CH2:2][CH2:3][CH3:4]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[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][CH2:22]/[CH:23]=[CH:24]\[CH2:25][N:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[CH:16]=2)=[C:7]([NH:31][C:32]([NH:34][C:35]2[C:40]([CH:41]([CH3:43])[CH3:42])=[CH:39][CH:38]=[CH:37][C:36]=2[CH:44]([CH3:46])[CH3:45])=[O:33])[C:6]1=[O:47])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 22106143HCID 22106143, compound

Product 1

HCID 67552825HCID 67552825, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A suspension of N-[1-butyl-4-[3-{(4-diethylamino-2-butynyl)oxy}-phenyl]-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (300 mg, 0.45 mmol), a Lindlar catalyst (distributed by Sigma Alderich Japan, 20 mg) in methanol (20 ml) was stirred at room temperature under hydrogen atmosphere for six hours. The mixture was filtered through a cerite pad, and the filtrate was concentrated under reduced pressure. The resultant was dissolved in chloroform, and the mixture was washed with a dilute aqueous ammonia, washed with water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3-8% methanol in chloroform) to give the title compound (280 mg, 0.43 mmol).

Workup

  1. filtrationThe mixture was filtered through a cerite pad
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe resultant was dissolved in chloroform
  4. washthe mixture was washed with a dilute aqueous ammonia
  5. washwashed with water
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (3-8% methanol in chloroform)

Sources & evidence

ORD record
ord-e52c66be39824055854d43b9ce1ba7de
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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