Sodium Carbonate → HCID 69332626, 화합물

HRID 915060노트

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HRID 915060 반응식
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[N:9]=[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:15]2[CH:16]=[CH:17][C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[N:20]=2)=[N:12][C:13]=1Br.CC1(C)C(C)(C)OB([C:39]2[CH:40]=[N:41][N:42](C(OC(C)(C)C)=O)[CH:43]=2)O1>O.O1CCOCC1.CC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:8]1[N:9]=[C:10]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:15]2[CH:16]=[CH:17][C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[N:20]=2)=[N:12][C:13]=1[C:39]1[CH:40]=[N:41][NH:42][CH:43]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

생성물 1

HCID 69332626HCID 69332626, 화합물수율 72.8%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 180Acetone용매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
102.5 °C

실험 절차

Under nitrogen atmosphere, a solution of sodium carbonate (330 mg) in water (2.4 ml) was added to a suspension of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (300 mg), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (573 mg) and tetrakis(triphenylphosphine)palladium (27 mg) in dioxane (6 ml) and the mixture was stirred at 100-105° C. for 4 hours. After addition of water (30 ml), a precipitate was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (10:90 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-[5-amino-3-phenyl-6-(1H-pyrazol-4-yl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (211 mg).

후처리

  1. filtrationa precipitate was collected by filtration
  2. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (10:90 v/v)
  3. customto give a solid
  4. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-e1b59348aa41433eb31169acf50d8fcd
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265120B2

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