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Diisopropylethylamine → 6-[2-Methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1678340
Notes
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Reaction equation

HRID 1678340 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:31][CH3:32])[CH:3]=1.[CH3:33][C:34]1[N:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](O)=[O:37].C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:32][O:31][C:4]1[CH:3]=[C:2]([O:1][C:36]([C:35]2[C:34]([CH3:33])=[N:42][CH:41]=[CH:40][CH:39]=2)=[O:37])[CH:7]=[CH:6][C:5]=1[C:8]1[C:9]([CH2:21][NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]2[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6433732-Methylnicotinic acidHCID 25015626HCID 25015626, compound

Product 1

HCID 247987996-[2-Methoxy-4-(2-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 65%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-(4-hydroxy-2-methoxyphenyl)-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 4-1, 25.0 mg, mmol), 2-methylnicotinoic acid (8.0 mg, 0.058 mmol), N,N-diisopropylethylamine (20.2 μL, 0.116 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (24.3 mg, mmol) was dissolved in anhydrous N,N-dimethylformamide (0.5 mL), and then the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (70 mL). The mixture was washed with water (70 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (20.7 mg) as a colorless solid. (Yield 65%)

Workup

  1. washThe mixture was washed with water (70 mL) and saturated brine (50 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b81692b0fd704e8ea28516374865cfcf
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008498B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes