2-Methoxyethylamine → HCID 89606104, compound

HRID 1430434Notes

Reaction equation

HRID 1430434 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13](Cl)[CH:12]=3)[CH:7]=1.[CH3:24][O:25][CH2:26][CH2:27][NH2:28]>O1CCOCC1>[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:28][CH2:27][CH2:26][O:25][CH3:24])[CH:12]=3)[CH:7]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 87666922HCID 87666922, compound

Product 1

HCID 89606104HCID 89606104, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of Example A6 (0.500 g, 1.507 mmol) in dioxane (10 mL) was added 2-methoxyethylamine (2 mL, 23.22 mmol) and the mixture was heated at 100° C. for 40 h. Solvent from the reaction mixture was evaporated and the residue was diluted with water (50 mL) and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried, and the solvent evaporated to provide 3-(5-amino-4-fluoro-2-methylphenyl)-1-ethyl-7-(2-methoxyethylamino)-1,6-naphthyridin-2(1H)-one (405 mg, 73% yield) as an orange-yellow solid. MS (ESI) m/z: 371.2 [M+H]+.

Workup

  1. customSolvent from the reaction mixture was evaporated
  2. additionthe residue was diluted with water (50 mL)
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-bbdc4c70d86f4185bac059232f4c67ec
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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