Water → 3-[2-Amino-3-(2-chloro-4-pyridinyl)imidazo[1,2-b]pyridazin-7-yl]-N-methylbenzamide

HRID 1097311노트

반응식

HRID 1097311 반응식
COC(=O)[NH:4][C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:22])[NH:20][CH3:21])[CH:14]=3)[CH:10]=[N:9][N:8]2[C:23]=1Br.[Cl:26][C:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[CH:29][N:28]=1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:4][C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=3)[C:19]([NH:20][CH3:21])=[O:22])[CH:10]=[N:9][N:8]2[C:23]=1[C:31]1[CH:30]=[CH:29][N:28]=[C:27]([Cl:26])[CH:32]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 59443497N-[3-bromo-7-[3-[(methylamino)carbonyl]phenyl]imidazo[1,2-b]pyridazin-2-yl]carbamic acid methyl ester

생성물 1

HCID 594435023-[2-Amino-3-(2-chloro-4-pyridinyl)imidazo[1,2-b]pyridazin-7-yl]-N-methylbenzamide

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

[3-Bromo-7-(3-Methylcarbamoyl-phenyl)-imidazo-[1,2-b]-pyridazin-2-yl]-carbamic acid methyl ester (1 eq, 0.159 mmol, 65 mg) and 2-chloropyridine-4-boronic acid (1.2 eq, 0.191 mmol, 30.1 mg) are dissolved in DME (3 ml) and water (0.75 ml) and Na2CO3 (3 eq, 0.478 mmol, 50.6 mg) is added. PdCl2(PPh3)2 (0.05 eq, 0.008 mmol, 5.59 mg) is then added and the reaction mixture is heated using microwave radiation at 120° C. for 50 min. At the completion of this time the solvent is evaporated and the reaction mixture is dissolved in MeOH, filtered and the solvent is removed in vacuo to yield 3-[2-Amino-3-(2-Chloro-pyridin-4-yl)-imidazo -[1,2-b]-pyridazin-7-yl]-N-methyl benzamide as a yellow solid; [M+H]+=379

후처리

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 50 min
  4. customAt the completion of this time the solvent is evaporated
  5. dissolutionthe reaction mixture is dissolved in MeOH
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-a76d6e87fc2e4e3ea7671be3a9a2428f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143253B2

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