Methanol → 6-chloro-2-(4-fluorophenyl)-8-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine

HRID 1035786노트

반응식

HRID 1035786 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:36])[C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[N:24](S(C5C=CC=CC=5)(=O)=O)[CH:25]=[CH:26][C:19]=34)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.CO.O1CCCC1.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:36])[C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[NH:24][CH:25]=[CH:26][C:19]=34)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:10]=2)[N:7]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 468994996-chloro-2-(4-fluorophenyl)-8-methyl-3-[1-(phenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine

생성물 1

HCID 468995006-chloro-2-(4-fluorophenyl)-8-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine수율 80%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Added to a suspension of 0.50 g (0.97 mmol) of 6-chloro-2-(4-fluorophenyl)-8-methyl-3-[1-(phenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine in 10 ml of a mixture of methanol and a few ml of tetrahydrofuran is 0.32 ml (1.9 mmol) of a 6N aqueous solution of sodium hydroxide. The mixture gradually become homogeneous and the reaction is stirred for 30 minutes. The reaction medium is diluted with 100 ml of water and the product is extracted with dichloromethane. The organic phase is separated, dried over sodium sulphate and the solvent is removed by evaporation under reduced pressure. The orange solid obtained is then chromatographed over a silica gel column (35 g) by eluting with a mixture of dichloromethane, methanol and aqueous ammonia (95/5/0.5) in order to give 0.293 g of 6-chloro-2-(4-fluorophenyl)-8-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)imidazo[1,2-b]pyridazine in the form of a yellow powder after trituration in isopropyl ether, chilling, filtration and drying.

후처리

  1. extractionthe product is extracted with dichloromethane
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed by evaporation under reduced pressure
  5. customThe orange solid obtained
  6. customis then chromatographed over a silica gel column (35 g)
  7. washby eluting with a mixture of dichloromethane, methanol and aqueous ammonia (95/5/0.5) in order

출처 및 근거

ORD 기록
ord-85e6e718ada247c09cf64b80f959646c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546395B2

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