Thioglycolic Acid → 1-Ethyl-3,3,5-trimethyl-7-{3-[2-(1-oxo-1H-isoquinolin-2-yl)ethylamino]propyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68988노트

반응식

HRID 68988 반응식
[OH-].[Li+].C(O)(=O)CS.CN(C=O)C.[CH2:13]([N:15]1[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[C:19](=[O:25])[N:18]([CH3:26])[C:17]2[CH:27]=[C:28]([CH2:31][CH2:32][CH2:33][N:34]([CH2:47][CH2:48][N:49]3[CH:58]=[CH:57][C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:50]3=[O:59])S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH:29]=[CH:30][C:16]1=2)[CH3:14]>O>[CH2:13]([N:15]1[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[C:19](=[O:25])[N:18]([CH3:26])[C:17]2[CH:27]=[C:28]([CH2:31][CH2:32][CH2:33][NH:34][CH2:47][CH2:48][N:49]3[CH:58]=[CH:57][C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:50]3=[O:59])[CH:29]=[CH:30][C:16]1=2)[CH3:14]

참가 물질

6

반응물 4

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 6228DimethylformamideHCID 66960684HCID 66960684, 화합물

생성물 1

HCID 706569721-Ethyl-3,3,5-trimethyl-7-{3-[2-(1-oxo-1H-isoquinolin-2-yl)ethylamino]propyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione수율 68.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Lithium hydroxide (3.2 g), and thioglycolic acid (2.4 ml) were added to a DMF solution (27.4 ml) of N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl)propyl]-2-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]benzenesulfonamide (4.56 g). The mixture was stirred at room temperature for 1 hour. The reaction mixture was condensed under reduced pressure. Water was added to the residue, followed by extraction using dichloromethane. The organic layer was washed with water and saturated saline, dried with magnesium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1). The purified product was condensed under reduced pressure to produce the title compound (2.24 g) as a yellow oil.

후처리

  1. customcondensed under reduced pressure
  2. extractionfollowed by extraction
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried with magnesium sulfate, and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1)
  6. customcondensed under reduced pressure

출처 및 근거

ORD 기록
ord-badb09cd37d441ab95f32fa66d52b37c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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