Potassium Carbonate → 1-{2-[6-Methoxy-4-(2-methyl-[1,8]naphthyridin-3-yloxy)-quinolin-7-yloxy]-ethyl}-piperidine 4-ol

HRID 229076Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[C:17]([CH3:26])=[N:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].[OH:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>CN(C)C=O>[CH3:28][O:27][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[O:4][CH2:3][CH2:2][N:39]1[CH2:40][CH2:41][CH:36]([OH:35])[CH2:37][CH2:38]1)[N:12]=[CH:11][CH:10]=[C:9]2[O:15][C:16]1[C:17]([CH3:26])=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][N:20]=2

Participants

Conditions

Temperature: 80 °C

Procedure

3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine (compound 398) (32 mg) was suspended in N,N-dimethylformamide (2 ml). Potassium carbonate (34 mg) and 4-hydroxypiperidine (25 mg) were added to the suspension, and the mixture was stirred at 80° C. overnight. The solvent was removed by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (22 mg, yield 60%).

Workup

customThe solvent was removed by distillation under the reduced pressure, water
additionwas then added to the residue
extractionthe mixture was extracted with chloroform
washThe chloroform layer was washed with saturated brine
dry with materialwas dried over anhydrous sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-ab74a78b904749109a7ce27df810a439
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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