1,2-Ethanediamine, N1,N1,N2-trimethyl- → 6-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1678344Notes

Reaction equation

HRID 1678344 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][N:22]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[O:46][CH3:47])C(OCC3C4C=CC=CC=4C4C3=CC=CC=4)=O)=[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:48][CH3:49])[CH:3]=1.[C:50](N1C=CN=C1)(N1C=CN=C1)=[O:51].[CH3:62][N:63]([CH3:68])[CH2:64][CH2:65][NH:66][CH3:67]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:62][N:63]([CH3:68])[CH2:64][CH2:65][N:66]([C:50]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][NH:22][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[O:46][CH3:47])=[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:48][CH3:49])[CH:3]=1)=[O:51])[CH3:67]

Participants

6

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 682631,1'-CarbonyldiimidazoleHCID 669929016-(4-Hydroxy-2-methoxyphenyl)-5-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 579906306-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(4-hydroxy-2-methoxyphenyl)-5-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 5, 25.0 mg, 0.0383 mmol), 1,1′-carbonyldiimidazole (62.0 mg, 0.382 mmol) and 4-dimethylaminopyridine (0.5 mg, 0.004 mmol) was dissolved in anhydrous tetrahydrofuran (1 mL), and then the solution was stirred at room temperature for 4.5 hours. N,N,N′-trimethylethylenediamine (39.2 mg, 0.383 mmol) was added thereto, and then the mixture was stirred at 60° C. for 2 hours. The reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate). The obtained colorless amorphous product was dissolved in N,N-dimethylformamide (1 mL), and then piperidine (50 μL) was added thereto. After the reaction mixture was stirred at room temperature for 15 minutes, it was diluted with ethyl acetate (20 mL). The mixture was washed with water (15 mL) and saturated brine (15 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 mg) as a colorless amorphous product. (Yield 47%)

Workup

  1. stirringthe mixture was stirred at 60° C. for 2 hours
  2. customThe reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate)
  3. dissolutionThe obtained colorless amorphous product was dissolved in N,N-dimethylformamide (1 mL)
  4. additionpiperidine (50 μL) was added
  5. stirringAfter the reaction mixture was stirred at room temperature for 15 minutes
  6. additionit was diluted with ethyl acetate (20 mL)
  7. washThe mixture was washed with water (15 mL) and saturated brine (15 mL) successively
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5bab604486894eb6885bfb416befa635
Source dataset
uspto-grants-2011_08
Patent number
US08008498B2

Reaction notes

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