HCID 16110249, compound → HCID 16110251, compound

HRID 896429Notes

Reaction equation

HRID 896429 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH2:15]([CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:32])[C:29](Cl)=[O:30])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)(Cl)Cl>[CH2:15]([CH:22]1[CH2:23][CH2:24][N:25]([C:28](=[O:32])[C:29]([NH:1][C:2]2[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]3[NH:6][C:7](=[O:9])[O:8][C:4]=3[CH:3]=2)=[O:30])[CH2:26][CH2:27]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 16110249HCID 16110249, compoundHCID 16110250HCID 16110250, compound

Product 1

HCID 16110251HCID 16110251, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 3.23 g (16.56 mmol) of 6-amino-5-nitro-3H-benzoxazole-2-one (step a), 2.58 ml (18.5 mmol) of trethylamine and 100 ml of chloroform 5.25 g (19.75 mmol) of (4-benzylpiperidin-1-yl)oxoacetyl chloride in 20 ml of chloroform is added dropwise at 20° C., then the mixture is stirred at room temperature for 2 h. The mixture is washed with water, the organic layer is dried and concentrated. The residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and toluene:methanol=4:1 as eluent to yield 3.3 g (47%) of the title compound. Mp.: foam.

Workup

  1. washThe mixture is washed with water
  2. customthe organic layer is dried
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-98144ccc7ed8458d8d7895faee5e9713
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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