Tetrahydrofuran → 8-(2-Methoxyphenylaminomethyl)-7-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038506

反応式

HRID 1038506 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([CH2:18][N:19]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])C(OCC3C4C=CC=CC=4C4C3=CC=CC=4)=O)=[C:16]3[C:11]([NH:12][C:13]([CH3:48])([CH3:47])[C:14](=[O:46])[N:15]3[CH3:45])=[CH:10][CH:9]=2)=[C:4]([O:49][CH3:50])[CH:3]=1.[CH2:51]([N:53](CC)[CH2:54]C)C.Cl.[Cl-].[O:60]1[CH2:64][CH2:63][CH2:62][CH2:61]1>ClCCl>[CH3:44][O:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[NH:19][CH2:18][C:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:64]([C:63]3[CH:51]=[N:53][CH:54]=[CH:61][CH:62]=3)=[O:60])=[CH:3][C:4]=2[O:49][CH3:50])=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH3:45])[C:14](=[O:46])[C:13]([CH3:48])([CH3:47])[NH:12]2

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 6410751Hydrogen chloride dimerHCID 583372217-(4-Hydroxy-2-methoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

生成物 1

HCID 576718608-(2-Methoxyphenylaminomethyl)-7-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

7-(4-Hydroxy-2-methoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 13-1, 30.0 mg, 0.0448 mmol) was dissolved in mixed solvent of tetrahydrofuran (1 mL) and dichloromethane (1 mL), and triethylamine (25 μL, 0.18 mmol) and nicotynoyl chloride hydrochloride (12.0 mg, 0.0674 mmol) were added successively. After the reaction mixture was stirred for 40 minutes at room temperature, it 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 for 20 minutes at room temperature, it was diluted with ethyl acetate (50 mL). The mixture was washed with water (50 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 (13.0 mg) as a colorless solid. (Yield 52%)

後処理

  1. additionwere added successively
  2. customit 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 for 20 minutes at room temperature
  6. additionit was diluted with ethyl acetate (50 mL)
  7. washThe mixture was washed with water (50 mL) and saturated brine (50 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-d6023f04b96b43edabec62b7308f6361
出典データセット
uspto-grants-2013_10
特許番号
US08551991B2

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