Dimethylformamide → N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]-2-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]benzenesulfonamide

HRID 1183095노트

반응식

HRID 1183095 반응식
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.I[CH2:13][CH2:14][CH2:15][N:16]([CH2:29][CH2:30][N:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27])(=[O:19])=[O:18].[CH2:42]([N:44]1[C:50](=[O:51])[C:49]([CH3:53])([CH3:52])[C:48](=[O:54])[N:47]([CH3:55])[C:46]2[CH:56]=[C:57]([OH:60])[CH:58]=[CH:59][C:45]1=2)[CH3:43]>C(OCC)(=O)C>[CH2:42]([N:44]1[C:50](=[O:51])[C:49]([CH3:53])([CH3:52])[C:48](=[O:54])[N:47]([CH3:55])[C:46]2[CH:56]=[C:57]([O:60][CH2:13][CH2:14][CH2:15][N:16]([CH2:29][CH2:30][N:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]3=[O:41])[S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-:28])=[O:27])(=[O:19])=[O:18])[CH:58]=[CH:59][C:45]1=2)[CH3:43]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68673067HCID 68673067, 화합물HCID 686733851-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

생성물 1

HCID 68675475N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]-2-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]benzenesulfonamide수율 69.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.22 g, 1.6 mmol) was added to a DMF solution (10 ml) of N-(3-iodopropyl)-2-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]benzenesulfonamide (0.57 g, 1.05 mmol) and 1-ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.33 g, 1.26 mmol), and stirred at room temperature overnight. The reaction mixture was added to ice water, and extraction with ethyl acetate was performed. The organic layer was washed with 1N-sodium hydroxide aqueous solution and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 0.49 g (yield: 69%) of N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]-2-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]benzenesulfonamide as a white amorphous solid.

후처리

  1. washThe organic layer was washed with 1N-sodium hydroxide aqueous solution and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-f7f20472d4f249008d14e5a6788f7a72
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664217B2

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