HCID 67352504, compound → HCID 67350133, compound

HRID 1672755Notes

Reaction equation

HRID 1672755 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[CH2:14][CH:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:28]=1)[CH3:2].[H][H]>C(O)C.C1COCC1.[Pd]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:15]2[CH2:14][CH:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]3[N:28]=[C:4]([NH:3][CH2:1][CH3:2])[N:5]=[CH:6][C:7]=3[C:16]2=[O:17])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 67352504HCID 67352504, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67350133HCID 67350133, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Compound 5 (0.496 g, 1.30 mmol) obtained in Example 5 was dissolved in ethanol/THF=5/1 (12 mL), and the mixture was stirred under a stream of hydrogen gas for 2 hours after adding 10% palladium-on-carbon (Pd—C) (50% water, 276 mg, 0.130 mmol). Insolubles were separated by filtration through sellite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (Compound 6) (0.410 g, 90%).

Workup

  1. customInsolubles were separated by filtration through sellite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2b32e68ca0fd4f9996383863bffe40cd
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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