HCID 86757560, compound → HCID 21352706, compound

HRID 427559Notes

Reaction equation

HRID 427559 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[C:7]([NH:9][C:10]1[C:11]([NH:16][C:17]([O:19][CH:20](C2CCNCC2)[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:8])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][CH:35]=1)[C:7]([NH:9][C:10]1[C:11]([NH:16][C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:23][CH2:22]2)=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

4

Reactant 1

HCID 86757560HCID 86757560, compound

Product 1

HCID 21352706HCID 21352706, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N1-(3-nitrobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine (370 mg, 0.78 mmol) and 5% palladium-on-carbon (200 mg) in ethanol (10 mL) was placed under an atmosphere of hydrogen (1 atm). After consumption of the starting material, the mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. Recrystallization (methanol/diethyl ether) yielded 40 mg (12%) of the title compound.

Workup

  1. customAfter consumption of the starting material
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. concentrationthe filtrate concentrated in vacuo
  4. customRecrystallization (methanol/diethyl ether)

Sources & evidence

ORD record
ord-bc2b8d9c32b346f383acec80ddb4e9f8
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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