Water → Ammonia

HRID 870541Notes

Reaction equation

HRID 870541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[N:20]3)=[C:15](OS(C(F)(F)F)(=O)=O)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N[C:32]1[CH:33]=[CH:34][C:35](=[O:38])[NH:36][CH:37]=1.[CH:39]([NH:42]C(C)C)(C)C.O>CC(N(C)C)=O>[NH3:14].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[N:20]3)=[C:15]([NH:42][CH2:39][C:32]3[CH:33]=[CH:34][C:35](=[O:38])[NH:36][CH:37]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 81825633630-94-3HCID 58071952HCID 58071952, compound

Product 2

HCID 222AmmoniaHCID 53341032HCID 53341032, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

100 mg Trifluoro-methanesulfonic acid 7-(3,4,5-trimethoxy-phenyl)-[1,6]naphthyridine-5-yl ester (6.1) was placed in 3 mL dimethylacetamide at ambient temperature before 111 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. 1.3 mL N,N-Diisopropylamine was added and the reaction was heated to 100° C. overnight. After this time, the reaction was heated to 120° C. and stirred overnight. The mixture was then cooled to ambient temperature and water was added. The mixture was extracted into ethyl acetate (×3) and the combined organic fractions were washed with water, separated and the solvent was removed under reduced pressure. Purification by preparative HPLC and then by silica gel chromatography (ethyl acetate containing 1-10% of 7M ammonia in methanol) gave the title compound.

Workup

  1. additionwas added
  2. temperaturecooled to ambient temperature
  3. temperaturethe reaction was heated to 100° C. overnight
  4. temperatureAfter this time, the reaction was heated to 120° C.
  5. temperatureThe mixture was then cooled to ambient temperature
  6. extractionThe mixture was extracted into ethyl acetate (×3)
  7. washthe combined organic fractions were washed with water
  8. customseparated
  9. customthe solvent was removed under reduced pressure
  10. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-7420091921364b62870491a04702d868
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

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