Water → HCID 58071947, compound

HRID 715721Notes

Reaction equation

HRID 715721 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[C:13]([OH:21])[C:14]3[CH:15]=[CH:16][CH:17]=[N:18][C:19]=3[CH:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:22](=[O:25])([O-])[O-:23].[K+].[K+].Br[CH2:29][C:30]#[N:31].O.C[N:34](C)C=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[C:13]([O:21][CH2:29][C:30]3[O:23][C:22](=[O:25])[NH:34][N:31]=3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 178488435HCID 178488435, compound

Product 1

HCID 58071947HCID 58071947, compound

Conditions

Temperature
60 °C

Procedure

1 g 7-(3,4-Dimethoxy-phenyl)-[1,6]naphthyridine-5-ol (5.31) was placed in 20 mL N,N-dimethylformamide at ambient temperature before 2.45 g potassium carbonate was added. The reaction was stirred for 10 min at ambient temperature before 0.74 mL bromoacetonitrile was introduced. The reaction was heated to 60° C. under an atmosphere of nitrogen for 4 h. After this time, the reaction was cooled to ambient temperature and water was added. The mixture was extracted with ethyl acetate (×2) and the combined organic fractions were washed with water (×2), saturated sodium chloride solution, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. Purification by chromatography on silica gel (tert-butyl methyl ether/ethyl acetate: 100:0 to 0:100) provided the title compound.

Workup

  1. additionwas added
  2. additionwas introduced
  3. temperatureAfter this time, the reaction was cooled to ambient temperature
  4. extractionThe mixture was extracted with ethyl acetate (×2)
  5. washthe combined organic fractions were washed with water (×2), saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customPurification by chromatography on silica gel (tert-butyl methyl ether/ethyl acetate: 100:0 to 0:100)

Sources & evidence

ORD record
ord-cf9009d02db849f89dcd202982617319
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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