HCID 16110251, compound → HCID 16110265, compound

HRID 902155Notes

Reaction equation

HRID 902155 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[C:15]([NH:17][C:18]2[C:27]([N+:28]([O-])=O)=[CH:26][C:21]3[NH:22][C:23](=[O:25])[O:24][C:20]=3[CH:19]=2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[NH2:28][C:27]1[C:18]([NH:17][C:15](=[O:16])[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]2)=[O:31])=[CH:19][C:20]2[O:24][C:23](=[O:25])[NH:22][C:21]=2[CH:26]=1

Participants

4

Reactant 1

HCID 16110251HCID 16110251, compound

Product 1

HCID 16110265HCID 16110265, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.3 g (7.7 mmol) of 2-(4-benzylpiperidin-1-yl)-N-(5-nitro-2-oxo-2,3-dihydro-benzoxazol-6-yl)-2-oxo-acetamide, 100 ml of methanol and 0.3 g of 10% Pd/C catalyst is hydrogenated for 8 h. The catalyst is filtered off and the filtrate is concentrated. The residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and toluene:acetone=2:1 as eluent to yield 1.06 g (34.5%) of the title compound. Mp.: 296° C. (toluene-acetone).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-e999428050ed436990f1959fde2a2bd0
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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