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

HRID 2115754
Notes
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Reaction equation

HRID 2115754 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 11430Potassium CarbonateHCID 59813676n-[6-((6,7-Dimethoxy-4-quinolyl)oxy) (2-naphthyl)](2-fluoro-3-pyridyl)carboxamide

Product 1

HCID 59813431n-(6-((6,7-Bis(methoxy)-4-quinolinyl)oxy)-2-naphthalenyl)-2-((2-(dimethylamino)ethyl)oxy)-3-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 8857
Ethyl Acetate
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

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

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

Sources & evidence

ORD record
ord-718238ed734e474d9e34ab3aebd14092
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07435823B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes