Dimethyl Sulfoxide → 3-({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)pyridine-2-carbaldehyde

HRID 68980

반응식

HRID 68980 반응식
I(C1C=CC=CC=1C(O)=O)(=O)=O.CS(C)=O.[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][N:36]([CH2:50][C:51]3[C:52]([CH2:57][OH:58])=[N:53][CH:54]=[CH:55][CH:56]=3)[CH2:37][CH2:38][N:39]3[CH:44]=[CH:43][C:42]4[O:45][C:46]([CH3:48])=[CH:47][C:41]=4[C:40]3=[O:49])[CH:33]=[CH:34][C:20]1=2)[CH3:18]>O>[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][N:36]([CH2:50][C:51]3[C:52]([CH:57]=[O:58])=[N:53][CH:54]=[CH:55][CH:56]=3)[CH2:37][CH2:38][N:39]3[CH:44]=[CH:43][C:42]4[O:45][C:46]([CH3:48])=[CH:47][C:41]=4[C:40]3=[O:49])[CH:33]=[CH:34][C:20]1=2)[CH3:18]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 1087942-Iodoxybenzoic acidHCID 669612451-Ethyl-7-({N-(2-hydroxymethylpyridin-3-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

생성물 1

HCID 888768503-({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)pyridine-2-carbaldehyde수율 60.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2-iodoxybenzoic acid (IBX, 0.235 g) was added to the dimethyl sulfoxide suspension (10 mL) of 1-ethyl-7-((N-((2-(hydroxymethyl)pyridin-3-yl)methyl)-N-(2-(2-methyl-4-oxofuro[3,2-c]pyridin-5(4H)-yl)ethyl)amino)methyl)-3,3,5-trimethyl-1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione (0.48 g) and the mixture was stirred overnight at room temperature. Water was added to the resulting mixture and then the mixture was extracted with ethyl acetate twice. The combined organic layer was concentrated under reduced pressure, and then the residue was purified by column-chromatography (ethyl acetate:hexanes=50:50→100:0). The purified product was recrystallized from ether to afford the titled compound as ivory powder (0.29 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified by column-chromatography (ethyl acetate:hexanes=50:50→100:0)
  4. customThe purified product was recrystallized from ether

출처 및 근거

ORD 기록
ord-b3e399c4d7394693a006696ab522c08e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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