Water → 6-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine

HRID 1865207

反応式

HRID 1865207 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[C:25]2[C:20](=[CH:21][C:22]([OH:26])=[CH:23][CH:24]=2)[N:19]([CH3:27])[N:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([NH2:16])=[N:18][N:19]2[CH3:27])=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 1357424603-amino-1-methyl-1H-indazol-6-ol

生成物 1

HCID 445622906-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-Chloro-6,7-dimethoxyquinoline (2.60 g, 11.7 mmol), 3-amino-1-methyl-1H-indazol-6-ol (Step a, 2.72 g, 16.7 mmol) and cesium carbonate (Aldrich, 16.3 g, 50.1 mmol) in DMSO (16.7 mL, Aldrich) were stirred at 100° C. for 16 h. After cooling to RT, water was added. The aqueous layer was extracted with DCM. The organic phase was washed with water, dried with MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography using 0-100% of a 90:10:1 (CH2Cl2:MeOH:NH4OH) solution as the eluant afforded the title compound as a white solid. MS (ESI, pos. ion) m/z: 351.1 (M+1). Mass Calc'd for C19H18N4O3: 350.38.

後処理

  1. extractionThe aqueous layer was extracted with DCM
  2. washThe organic phase was washed with water
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-28fd85ff5c9647d7a7a4b5d644a47efc
出典データセット
uspto-grants-2009_12
特許番号
US07626030B2

関連ノート

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