Morpholine → HCID 67464620, compound

HRID 1777724Notes

Reaction equation

HRID 1777724 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][CH:23]=[N:24]4)=[C:19](Cl)[N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][CH:23]=[N:24]4)=[C:19]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86682422HCID 86682422, compound2×

Product 1

HCID 67464620HCID 67464620, compoundYield 91%

Procedure

A flask charged with 7-(1-benzyl-1H-indol-4-yl)-5-chloro-1,6-naphthyridine, 3 (94 mg, 0.25 mmol, 1 eq) and morpholine (1.6 mL, 18 mmol, 70 eq) was heated at 100° C. overnight under Ar(g). Once cooled down, the solvent was removed in vacuo, and the residue was purified by silica gel column chromatography with hexane/EtOAc (3:2-0:1) to yield the product as pale yellow solid (96 mg, 91%).

Workup

  1. temperatureOnce cooled down
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by silica gel column chromatography with hexane/EtOAc (3:2-0:1)

Sources & evidence

ORD record
ord-cdcd00eb083c411e90a1f0c8301a31a9
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

Loading…