Dimethylformamide → HCID 57690994, compound

HRID 40374Notes

Reaction equation

HRID 40374 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([NH2:12])=[CH:7]2.CN(C=O)C.[H-].[Na+].Br[CH2:21][CH2:22][O:23][CH3:24]>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([NH:12][CH2:21][CH2:22][O:23][CH3:24])=[CH:7]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 576913478-Chloro-1,5-naphthyridin-3-amine

Product 1

HCID 57690994HCID 57690994, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask under nitrogen atmosphere was charged with 8-chloro-1,5-naphthyridin-3-amine (160 mg, 0.89 mmol), DMF (2.2 mL, 0.89 mmol). This was cooled to 0° C. and SODIUM HYDRIDE (60% dispersion in oil) (107 mg, 4.45 mmol) added portionwise. This was quickly followed by addition of 1-bromo-2-methoxyethane (0.12 mL, 1.25 mmol) dropwise via syringe. Ice bath removed and reaction mixture heated to 85° C. and stirred at this temperature for 16 hours. Reaction diluted with 5 mL of 5% MeOH/Dichloromethane, loaded onto silica gel column and eluted with 2% MeOH/DCM to afford 8-chloro-N-(2-methoxyethyl)-1,5-naphthyridin-3-amine (70 mg, 33% yield) as a light yellow solid.

Workup

  1. customIce bath removed
  2. customreaction mixture
  3. temperatureheated to 85° C.
  4. customReaction
  5. washeluted with 2% MeOH/DCM

Sources & evidence

ORD record
ord-950c7e016900471593a2c4c6e45a9233
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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