四氢呋喃 → 8-(2-Methoxyphenylaminomethyl)-7-[2-methoxy-4-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 872002笔记

反应方程式

HRID 872002 反应方程式
[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

参与物

6

反应物 4

HCID 8028四氢呋喃HCID 8471三乙胺HCID 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

产物 1

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

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

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%)

后处理

  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)

来源与证据

ORD记录
ord-cef1495e08044299bf14d03870ec8f16
来源数据集
uspto-grants-2015_03
专利号
US08975256B2

反应笔记

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