Water → 3-[2-{(1R*,2R*)-2-hydroxy-2-methylcyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine

HRID 965351

반응식

HRID 965351 반응식
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4][NH:3]1.[CH3:23][C:24]12[O:30][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]2.[OH-].[Na+].O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C1(C)C=CC=CC=1>[OH:30][C@:24]1([CH3:23])[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[N:3]1[C:2](=[O:1])[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4]1

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2242431-Methyl-1,2-epoxycyclohexaneHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

생성물 1

HCID 701575183-[2-{(1R*,2R*)-2-hydroxy-2-methylcyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine수율 6%

시약·촉매·용매 2

HCID 5963Benzyltrimethylammonium chloride촉매HCID 1140Toluene용매

실험 절차

A mixture of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.25 g), 1-methyl-1,2-epoxycyclohexane (1.31 g), benzyltrimethylammonium chloride (178 mg), 1N aqueous sodium hydroxide (7.8 ml), water (17 ml), and toluene was heated to reflux for 8 hours and 20 minutes. After the reaction mixture was cooled to room temperature, the precipitates were collected by filtration, washed with water, and dried. The crude material was purified by column chromatography on silica gel (CH2Cl2 :EtOAc=10:2) to give colorless crystals of 3-[2-{(1R*,2R*)-2-hydroxy-2-methylcyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine (189 mg).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours and 20 minutes
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe crude material was purified by column chromatography on silica gel (CH2Cl2 :EtOAc=10:2)

출처 및 근거

ORD 기록
ord-6e03ee8a66a946259afa79e1cb9fe6b6
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773530

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