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

HRID 872002

반응식

HRID 872002 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-cef1495e08044299bf14d03870ec8f16
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975256B2

연결된 노트

불러오는 중…