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 1968476ノート

反応式

HRID 1968476 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-(4-hydroxy-2-methoxyphenyl)-5-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)amino methyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 6, 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 mixture was stirred at room temperature for 4.5 hours. N,N,N′-Trimethylethylenediamine (39.2 mg, 0.383 mmol) was added thereto, 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 piperidine (50 μL) was added thereto. After the reaction mixture was stirred at room temperature for 15 minutes, the mixture 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 (9.9 mg) as a colorless amorphous product. (Yield 47%)

後処理

  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. additionthe mixture 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)

出典と根拠

ORDレコード
ord-9ab9df1221a844f58fab71c784915bca
出典データセット
uspto-grants-2013_04
特許番号
US08426406B2

反応ノート

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