Acetic Acid → 1-Ethyl-3,3,5-trimethyl-7-{[N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(2-morpholin-4-ylmethylbenzyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68983노트

반응식

HRID 68983 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([CH2:29][N:30]([CH2:44][C:45]3[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=3[CH:47]=O)[CH2:31][CH2:32][N:33]3[CH:38]=[CH:37][C:36]4[O:39][C:40]([CH3:42])=[CH:41][C:35]=4[C:34]3=[O:43])[CH:27]=[CH:28][C:14]1=2)[CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.ClCCCl>[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:21])([CH3:22])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([CH2:29][N:30]([CH2:31][CH2:32][N:33]3[CH:38]=[CH:37][C:36]4[O:39][C:40]([CH3:42])=[CH:41][C:35]=4[C:34]3=[O:43])[CH2:44][C:45]3[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=3[CH2:47][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:27]=[CH:28][C:14]1=2)[CH3:12]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 866704842-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)benzaldehyde

생성물 1

HCID 706564441-Ethyl-3,3,5-trimethyl-7-{[N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(2-morpholin-4-ylmethylbenzyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 962Water용매

실험 절차

Morpholine (0.06 ml) and acetic acid (0.1 ml) were added to a 1,2-dichloroethane solution (7 ml) of 2-({N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)benzaldehyde (0.35 g), and the mixture was stirred for 30 minutes at room temperature. Sodium triacetoxy borohydride (0.20 g) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction liquid, followed by extraction by dichloromethane. The organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=3:2). The purified product was condensed under reduced pressure to give the title compound (0.30 g) as a white amorphous solid.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction by dichloromethane
  3. dry with materialThe organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=3:2)
  5. customcondensed under reduced pressure

출처 및 근거

ORD 기록
ord-8521235ab2164157b2eed8381cd6ae6a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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