HCID 90449297, compound → HCID 89589800, compound

HRID 925515Notes

Reaction equation

HRID 925515 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][OH:13])=[C:5]2[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH:12]=[O:13])=[C:5]2[NH:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 90449297HCID 90449297, compound

Product 1

HCID 89589800HCID 89589800, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-((6-chloro-3-(hydroxymethyl)-1,5-naphthyridin-4-yl)amino)piperidine-1-carboxylate (0.39 g, 1 mmol) was dissolved in dichloromethane (10 mL), and to the solution added manganese dioxide (2.14 g, 32 mmol). The reaction mixture was stirred at room temperature for 3 h, filtered and the solid was washed with 30 mL of dichloromethane. The resulting wash liquid and the filtrate were combined and concentrated, and the resulting solid was recrystallized from methanol to give 0.311 g of a white solid.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with 30 mL of dichloromethane
  3. washThe resulting wash liquid
  4. concentrationconcentrated
  5. customthe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-17ecf0c40cd441c1ac31b8d5a91b4f77
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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