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

HRID 1865207

Reaction equation

HRID 1865207 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-28fd85ff5c9647d7a7a4b5d644a47efc
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Linked notes

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