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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Dimethylformamide → 2-(10-Fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-(4-methyl-5-oxo-6-(pyridin-3-ylamino)-4,5-dihydropyrazin-2-yl)nicotinaldehyde

HRID 1411714
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HRID 1411714 반응식
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:5][C:4](B(O)O)=[CH:3]1.Cl[C:20]1[C:25]([CH:26]=[O:27])=[C:24]([N:28]2[CH2:41][CH2:40][N:31]3[C:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C:37]=4[C:38]([F:39])=[C:30]3[C:29]2=[O:42])[N:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[F:39][C:38]1[C:37]2[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=2[N:31]2[CH2:40][CH2:41][N:28]([C:24]3[N:23]=[CH:22][CH:21]=[C:20]([C:4]4[N:5]=[C:6]([NH:9][C:10]5[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=5)[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=4)[C:25]=3[CH:26]=[O:27])[C:29](=[O:42])[C:30]=12
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 866842384-Chloro-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehydeHCID 866843344-Methyl-5-oxo-6-(pyridin-3-ylamino)-4,5-dihydropyrazin-2-ylboronic acid

생성물 1

HCID 866843352-(10-Fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-(4-methyl-5-oxo-6-(pyridin-3-ylamino)-4,5-dihydropyrazin-2-yl)nicotinaldehyde
수율 49.4%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

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온도
50 °C

실험 절차

A 50-mL round-bottomed flask equipped with a reflux condenser was charged with 186b (127 mg, 0.52 mmol), 4-chloro-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)nicotinaldehyde 134c (180 mg, 0.52 mmol), Na2CO3 (110 mg, 1.04 mmol), PdCl2(dppf) (38 mg, 0.052 mmol), DMF (12 mL), and water (1 mL). After bubbling nitrogen through the mixture for 30 minutes, it was heated at 50° C. for 8 hours under nitrogen. The reaction was then cooled to room temperature and concentrated under reduce pressure. The residue was purified by silica-gel column chromatography eluting with 30:1 methylene chloride/methanol to afford 186c (132 mg, 49%) as a brown solid. MS-ESI: [M+H]+ 514.3.

후처리

  1. customA 50-mL round-bottomed flask equipped with a reflux condenser
  2. customAfter bubbling nitrogen through the mixture for 30 minutes
  3. temperatureThe reaction was then cooled to room temperature
  4. concentrationconcentrated
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 30:1 methylene chloride/methanol

출처 및 근거

ORD 기록
ord-ace579c44cf54f34a90878e3668f5be5
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921353B2

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