2-(Dimethylamino)ethanol → n-(6-((6,7-Bis(methoxy)-4-quinolinyl)oxy)-2-naphthalenyl)-2-((2-(dimethylamino)ethyl)oxy)-3-pyridinecarboxamide

HRID 1925243Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH:26][C:27]([C:29]1[C:30](F)=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:28])[CH:20]=[CH:19]2.C([O-])([O-])=O.[K+].[K+].[CH3:42][N:43]([CH3:47])[CH2:44][CH2:45][OH:46]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH:26][C:27]([C:29]1[C:30]([O:46][CH2:45][CH2:44][N:43]([CH3:47])[CH3:42])=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:28])[CH:20]=[CH:19]2

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of N-[6-(6,7-dimethoxy-(4-quinolyloxy)) (2-naphthyl)](2-fluoro-(3-pyridyl))carboxamide (Step a, 62 mg, 0.13 mmol) and K2CO3 (166 mg, 1.3 mmol) in dry NMP (5 mL, Aldrich) was added N,N-dimethylethanolamine (35 mg, 0.36 mmol, Aldrich) at RT. The reaction was stirred at 110° C. for 16 h. The mixture was cooled and diluted with 60 mL of EtOAc, then washed with water and brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by prep-HPLC to give title compound as a white solid. MS (ESI, pos. ion) m/z: 539 (M+1). Mass Calc'd for C31H30N4O5: 538.22.

Workup

temperatureThe mixture was cooled
washwashed with water and brine
dry with materialThe organic phase was dried over MgSO4
concentrationconcentrated
customThe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-ba8a234edd4c422b93310233205bf586
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

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