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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
ノート
印刷プレビュー

反応式

HRID 873524 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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
収率 69.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7b591648ced84e31a5afe24e19e3ffee
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975263B2

反応ノート

読み込み中…

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