Methyl dichloroacetate → HCID 68089214, compound

HRID 1615664Notes

Reaction equation

HRID 1615664 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]1=[NH2+:12].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[Cl:26][CH:27]([Cl:32])[C:28](OC)=O.C(=O)([O-])[O-].[K+].[K+]>CCO>[Cl:26][CH:27]([Cl:32])[C:28]1[N:12]=[C:3]2[CH:4]=[CH:5][C:6]3[C:11]([N:2]2[N:1]=1)=[CH:10][CH:9]=[CH:8][N:7]=3

Participants

5

Reactant 3

HCID 8315Methyl dichloroacetateHCID 11430Potassium CarbonateHCID 178425985HCID 178425985, compound

Product 1

HCID 68089214HCID 68089214, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-amino-1,5-naphthyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (crude product from the previous step, 3.0 mmol), methyl 2,2-dichloroacetate (0.86 g, 6.0 mmol) and potassium carbonate (0.62 g, 4.5 mmol) in EtOH (30 mL) was stirred at 80° C. for 16 h. After cooled to room temperature, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluting with 2% v/v MeOH in DCM) to give the title compound as a purple solid (300 mg, yield 39%). ESI MS: m/z 253, 255 [M+H]+.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with 2% v/v MeOH in DCM)

Sources & evidence

ORD record
ord-bdcbb975415e480f8b894d29453e70b2
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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