Water → 3-(2-Amino-3-(2-phenyl-pyridin-4-yl)imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide

HRID 1097312노트

반응식

HRID 1097312 반응식
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])[CH:7]=[N:6][N:5]2[C:20]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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>[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])[CH:7]=[N:6][N:5]2[C:20]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 594435023-[2-Amino-3-(2-chloro-4-pyridinyl)imidazo[1,2-b]pyridazin-7-yl]-N-methylbenzamide

생성물 1

HCID 251747803-(2-Amino-3-(2-phenyl-pyridin-4-yl)imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

3-[2-Amino-3-(2-Chloro-pyridin-4-yl)-imidazo-[1,2-b]-pyridazin-7-yl]-N-methyl benzamide (1 eq, 0.146 mmol, 79 mg) and phenyl boronic acid (1.5 eq, 0.219 mmol, 27.5 mg) are dissolved in DME (1.5 ml) and water (0.4 ml) and Na2CO3 (3 eq, 0.438 mmol, 46.4 mg) are added. PdCl2(PPh3)2 (0.05 eq, 0.008 mmol, 5.12 mg) is then added and the reaction mixture is heated using microwave radiation at 120° C. for 15 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 3-(2-Amino-3-(2-phenyl-pyridin-4-yl)imidazo [1,2-b]pyridazin-7-yl]-N-methyl-benzamide as a yellow solid; [M+H]+=421

후처리

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 15 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

출처 및 근거

ORD 기록
ord-9fbc1249a4ae415d966e274d18469200
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143253B2

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