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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Ammonium Chloride → 9-{2-Methoxy-5-[6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2-yl]phenyl}-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

HRID 873524
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HRID 873524 반응식
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[OH:13][N:14]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH:31]3[C:44]4[C:43](=[O:45])[CH2:42][C:41]([CH3:47])([CH3:46])[CH2:40][C:39]=4[O:38][C:37]4[CH2:36][C:35]([CH3:49])([CH3:48])[CH2:34][C:33](=[O:50])[C:32]3=4)[CH:24]=2)[N:18]=1)[NH2:16].N12CCCN=C1CCCCC2.[Cl-].[NH4+]>C1COCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:15]3[NH:16][C:1](=[O:2])[O:13][N:14]=3)[N:18]=2)=[CH:24][C:25]=1[CH:31]1[C:32]2[C:33](=[O:50])[CH2:34][C:35]([CH3:49])([CH3:48])[CH2:36][C:37]=2[O:38][C:39]2[CH2:40][C:41]([CH3:46])([CH3:47])[CH2:42][C:43](=[O:45])[C:44]1=2
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참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137187592N'-hydroxy-6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboximidamide

생성물 1

HCID 137014752
9-{2-Methoxy-5-[6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2-yl]phenyl}-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
수율 69.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1,1′-Carbonyldiimidazole (173 mg, 1.07 mmol) was added to a solution of the N′-hydroxy-6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboximidamide produced in Example 8-1 (424 mg, 0.82 mmol) in THF (8.5 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 2 hours. Thereafter, 1,8-diazabicyclo[5.4.0]undec-7-ene (0.160 ml, 1.07 mmol) was added to the resulting solution, and the mixture thus obtained was then stirred for 4.5 hours. Subsequently, an aqueous solution of ammonium chloride was added to the reaction solution, and the mixed solution was then extracted with dichloromethane twice. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel thin-layer chromatography (methanol:dichloromethane=1:10, v/v). The solid thus obtained was washed with a mixed solution of diethyl ether and hexane, followed by collection by filtration and drying, to obtain the title compound (309 mg, yield: 69%).

후처리

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringwas then stirred for 4.5 hours
  4. extractionthe mixed solution was then extracted with dichloromethane twice
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customthe residue thus obtained
  9. customwas then purified by silica gel thin-layer chromatography (methanol
  10. customThe solid thus obtained
  11. washwas washed with a mixed solution of diethyl ether and hexane
  12. filtrationfollowed by collection by filtration
  13. customdrying

출처 및 근거

ORD 기록
ord-7b591648ced84e31a5afe24e19e3ffee
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975263B2

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