Water → HCID 21481011, compound

HRID 1490322Notes

Reaction equation

HRID 1490322 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:10][N:9]=[C:8]2[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:19][CH2:18]1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH2:41]Cl)[CH:36]=[CH:37][C:38]=1[O:39][CH3:40].O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]([CH2:41][C:35]1[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:33]([O:32][CH3:31])[CH:34]=1)[N:9]=[C:8]2[CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81740Veratryl chlorideHCID 178486923HCID 178486923, compound

Product 1

HCID 21481011HCID 21481011, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide was suspended 61.6 mg of sodium hydride at 0° C., and 590 mg of 5,6-dimethoxy-3-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]indazole was added thereto, followed by stirring for 30 minutes. To the mixture was added 290 mg of 3,4-dimethoxyphenylmethyl chloride. After 1.5 hours, 2.0 ml of water was added to the reaction mixture, followed by evaporation of the solvent. The residue was purified by silica gel column chromatography (chloroform:ethanol=20:1) and recrystallized from ethanol to yield 654 mg of the title compound.

Workup

  1. customat 0° C.
  2. waitAfter 1.5 hours
  3. customfollowed by evaporation of the solvent
  4. customThe residue was purified by silica gel column chromatography (chloroform:ethanol=20:1)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-02bbb85641b34669aae3d0c048375967
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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