Sodium Iodide → 1-(Cyclopropylmethyl)-5-(2-(2,3-Dihydro-1h-Imidazo[1,2-A]benzimidazol-1-Yl)ethoxy)-3-(1-Phenyl-1h-Pyrazol-5-Yl)pyridazin-4(1h)-One

HRID 333733노트

반응식

HRID 333733 반응식
[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([OH:11])[C:8](=[O:12])[C:7]([C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[CH:15][CH:14]=3)=[N:6]2)[CH2:3][CH2:2]1.Cl[CH2:25][CH2:26][N:27]1[C:31]2=[N:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N:30]2[CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(N(C)C)=O>[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([O:11][CH2:25][CH2:26][N:27]3[C:31]4=[N:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[N:30]4[CH2:29][CH2:28]3)[C:8](=[O:12])[C:7]([C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[CH:15][CH:14]=3)=[N:6]2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 7619001-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazoleHCID 895865391-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

생성물 1

HCID 566541311-(Cyclopropylmethyl)-5-(2-(2,3-Dihydro-1h-Imidazo[1,2-A]benzimidazol-1-Yl)ethoxy)-3-(1-Phenyl-1h-Pyrazol-5-Yl)pyridazin-4(1h)-One수율 62.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

A suspension of 1-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (231 mg), 1-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (249 mg), cesium carbonate (428 mg) and sodium iodide (253 mg) in dimethylacetamide (10 mL) was stirred at 80° C. for 13 hr. The reaction mixture was filtered and an insoluble material was separated and washed with ethyl acetate. The filtrate and the washing were combined, and concentrated under reduced pressure to dryness. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (231 mg) as a white amorphous powder.

후처리

  1. filtrationThe reaction mixture was filtered
  2. customan insoluble material was separated
  3. washwashed with ethyl acetate
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-9509177f140b41a781c4c27e390e6b49
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883788B2

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