Morpholine → HCID 11596751, compound

HRID 1839381Notes

Reaction equation

HRID 1839381 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:25])[CH:7]=[C:8]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:26])[CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCOCC1>[CH3:26][C:4]1[CH:3]=[C:2]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:11]=[C:10]2[C:5]=1[C:6](=[O:25])[CH:7]=[C:8]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:9]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 21948152HCID 21948152, compound

Product 1

HCID 11596751HCID 11596751, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-chloro-5-methyl-1-phenyl-2-phenylamino-1H-[1,8]naphthyridin-4-one (68.3 mg, 0.189 mmol) and morpholine (0.05 mL, 0.48 mmol) in dioxane (3 mL) was heated to 80° C. for 2 d. The reaction was cooled, concentrated in vacuo, diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo to give 5-methyl-7-morpholin-4-yl-1-phenyl-2-phenylamino-1H-[1,8]naphthyridin-4-one (67 mg, 92%) as yellow solid:

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ae91aa404f448c18d10212f51bc8883
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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