Hydrochloric Acid → HCID 22106351, compound

HRID 1456383Notes

Reaction equation

HRID 1456383 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)=[C:14]([NH:30][C:31]([NH:33][C:34]2[C:39]([CH:40]([CH3:42])[CH3:41])=[CH:38][CH:37]=[CH:36][C:35]=2[CH:43]([CH3:45])[CH3:44])=[O:32])[C:13]1=[O:46])C1C=CC=CC=1.Cl>C(O)C.[C].[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)=[C:14]([NH:30][C:31]([NH:33][C:34]2[C:39]([CH:40]([CH3:42])[CH3:41])=[CH:38][CH:37]=[CH:36][C:35]=2[CH:43]([CH3:45])[CH3:44])=[O:32])[C:13]1=[O:46]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22106130HCID 22106130, compound

Product 1

HCID 22106351HCID 22106351, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[1-(3-benzyloxypropyl)-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (1.31 g, 2.12 mmol) in ethanol (80 ml) was added 10% palladium-carbon (150 mg), and the mixture was stirred at room temperature under hydrogen atmosphere for three hours. To the mixture was added 12N hydrochloric acid (1 ml), and the mixture was further stirred at room temperature under hydrogen atmosphere for two hours. The mixture was filtered through a cerite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1-3% methanol in chloroform) to give the title compound (1.12 g, 2.12 mmol).

Workup

  1. stirringthe mixture was further stirred at room temperature under hydrogen atmosphere for two hours
  2. filtrationThe mixture was filtered through a cerite pad
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (1-3% methanol in chloroform)

Sources & evidence

ORD record
ord-2388f2204ab2499a8b632e5bdb172f62
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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