Morpholine → HCID 53482992, compound

HRID 1777711Notes

Reaction equation

HRID 1777711 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=2[O:20][CH3:21])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:21][O:20][C:13]1[C:14]([O:18][CH3:19])=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[CH:9]=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:11]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86682417HCID 86682417, compound

Product 1

HCID 53482992HCID 53482992, compound

Procedure

A solution of 5-chloro-7-(2,3-dimethoxy-phenyl)-[1,6]naphthyridine 3 (50 mg, 0.17 mmol, 1 eq) in morpholine (1.02 mL, 11.7 mmol, 68 eq) was heated up at 100° C. for 5 h under Ar(g). Once cooled down, the solution was subsequently partitioned and extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:2) to furnish the product, A, as a pale yellow solid (48 mg, 81%).

Workup

  1. temperatureOnce cooled down
  2. customthe solution was subsequently partitioned
  3. extractionextracted with CH2Cl2 (3×5 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (1:2)
  7. customto furnish the product

Sources & evidence

ORD record
ord-e96f53ac7b8a454193d9d3cd4c690873
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

Loading…