Dimethylacetamide → HCID 58071932, compound

HRID 870548Notes

Reaction equation

HRID 870548 reaction equation
[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](OS(C(F)(F)F)(=O)=O)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N[C:30]1[CH:31]=[CH:32][C:33](=[O:36])[NH:34][CH:35]=1.C[C:38]([N:40](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]([NH:40][CH2:38][C:30]3[CH:31]=[CH:32][C:33](=[O:36])[NH:34][CH:35]=3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 81825633630-94-32×HCID 58071886HCID 58071886, compound

Product 1

HCID 58071932HCID 58071932, compound

Conditions

Temperature
70 °C

Procedure

100 mg Trifluoromethanesulfonic acid 7-(3,4-dimethoxy-phenyl)-[1,6]naphthyridine-5-yl ester (6.2) was placed in 2 mL dimethylacetamide at ambient temperature before 120 mg 5-amino-1H-pyridine-2-one (2.31) was added. The reaction was heated to 70° C. overnight and then cooled to ambient temperature. After this time, additional 14.9 mg 5-amino-1H-pyridin-2-one (2.31) was added and the reaction was heated to 70° C. for 24 h and then 100° C. for a further 24 h. The solvent was removed under reduced pressure and the crude material was purified twice by silica gel chromatography (ethyl acetate/methanol) and then by preparative chromatography. Finally it was free-based using a SCX column to give the title compound.

Workup

  1. additionwas added
  2. temperaturecooled to ambient temperature
  3. temperaturethe reaction was heated to 70° C. for 24 h
  4. customThe solvent was removed under reduced pressure
  5. customthe crude material was purified twice by silica gel chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-940da1e3a1424eb99f2c41a4b152fd1e
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

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