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 1678344노트

반응식

HRID 1678344 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-5bab604486894eb6885bfb416befa635
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008498B2

반응 노트

불러오는 중…