Acetaldehyde → HCID 44562291, compound

HRID 1865208

Reaction equation

HRID 1865208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([NH2:26])=[N:21][N:22]2[CH3:25])=[CH:18][CH:17]=1.[CH:27](=O)[CH3:28]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([NH:26][CH2:27][CH3:28])=[N:21][N:22]2[CH3:25])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 445622906-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine

Product 1

HCID 44562291HCID 44562291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-((6,7-bis(methyloxy)-4-quinolinyl)oxy)-1-methyl-1H-indazol-3-amine (Example 120, 140 mg, 0.40 mmol) in dry DCM (Aldrich, 4.0 mL) at RT were added acetaldehyde (Aldrich, 21.1 mg, 0.48 mmol) followed by NaHB(OAc)3 (Aldrich, 102 mg, 0.48 mmol). After being stirred for 4 h at RT, the reaction was quenched by addition of water. The aqueous layer was extracted with DCM. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (DCM/acetone: 100/0 to 60/40) afforded the title compound. MS (ESI, pos. ion) m/z: 379.3 (M+1). Mass Calc'd for C21H22N4O3: 378.43.

Workup

  1. customthe reaction was quenched by addition of water
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (DCM/acetone: 100/0 to 60/40)

Sources & evidence

ORD record
ord-3bfd345eb81840b485ef73f474b63ded
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Linked notes

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