Potassium Carbonate → 4-Chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline

HRID 7491노트

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HRID 7491 반응식
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[N:18][CH:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:8][C:9]3[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=3)=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[N:18][CH:17]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 7365362-(chloromethyl)-1-methyl-1H-imidazoleHCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

생성물 1

HCID 219910194-Chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline수율 29%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
40 °C

실험 절차

The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for the starting material in Example 10), in DMF (6 ml). After stirring overnight at 40° C. the mixture was diluted with water and adjusted to pH7. After extraction with ethyl acetate the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/methanol (98/2) as eluent to give 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (111 mg, 29%).

후처리

  1. custom(prepared
  2. extractionAfter extraction with ethyl acetate the organic layer
  3. washwas washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-a2793211692d4541affe62f1da13a23a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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