Cesium carbonate → 7-[2-(4-Benzyloxy-6-oxo-6H-pyridazin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

HRID 564186노트

반응식

HRID 564186 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[N:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:22]([O:26][C:27]([N:29]1[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][C:33]([CH2:39][CH2:40]I)=[CH:34][CH:35]=2)[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C>[C:22]([O:26][C:27]([N:29]1[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][C:33]([CH2:39][CH2:40][N:12]3[C:11](=[O:15])[CH:10]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:14]=[N:13]3)=[CH:34][CH:35]=2)[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 580428517-(2-iodoethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 598221075-(benzyloxy)pyridazin-3(2H)-one

생성물 1

HCID 670069227-[2-(4-Benzyloxy-6-oxo-6H-pyridazin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 245 mg (1.21 mmol) 5-benzyloxy-2H-pyridazin-3-one (preparation 5c) in 1.2 mL DMF is added 791 mg (2.43 mmol) cesium carbonate and after 15 min 470 mg (1.21 mmol) 7-(2-iodoethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (preparation 8). The reaction mixture is stirred overnight at RT and the precipitate is removed by filtration. The solvent is evaporated, the residue is dissolved in DMF and purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

후처리

  1. customthe precipitate is removed by filtration
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in DMF
  4. custompurified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

출처 및 근거

ORD 기록
ord-4658ae456c5c42aba38cfd9a9799c37f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067590B2

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