Sodium Iodide → N-[1-(3-methylbenzyl)-4-methyl-hexahydro-1H-1,4-diazepin-6-yl]-1-ethyl-1H-indazole-3-carboxamide

HRID 374105

Reaction equation

HRID 374105 reaction equation
[CH3:1][N:2]1[CH2:8][CH:7]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH3:22])[N:13]=2)=[O:11])[CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35]Cl>C(C(C)=O)C>[CH3:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][N:5]1[CH2:6][CH:7]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH3:22])[N:13]=2)=[O:11])[CH2:8][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12102m-Xylyl chlorideHCID 14999044N-(1-methylhexahydro-1H-1,4-diazepin-6-yl)-1-ethyl-1H-indazole-3-carboxamide

Product 1

HCID 14999045N-[1-(3-methylbenzyl)-4-methyl-hexahydro-1H-1,4-diazepin-6-yl]-1-ethyl-1H-indazole-3-carboxamideYield 78.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of N-(1-methylhexahydro-1H-1,4-diazepin-6-yl)-1-ethyl-1H-indazole-3-carboxamide (1.8 g), potassium carbonate (4.1 g), sodium iodide (0.9 g), 3-methylbenzyl chloride (0.85 g) and methyl ethyl ketone (100 ml) is refluxed with stirring for 6 hours. After cooling, the reaction mixture is filtered, and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel with elution of chloroform-methanol (20:1). Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound (1.9 g) as an oil. The free base thus obtained is converted to the fumarate of the title compound in a usual manner, m.p. 135°-137° C. (recrystallized from ethanol-diethyl ether).

Workup

  1. temperatureis refluxed
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel with elution of chloroform-methanol (20:1)
  6. additionFractions containing the title compound
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eeb7f51a35804c3b9b3dbd092fa9d37a
Source dataset
uspto-grants-1992_11
Patent number
US05166341

Linked notes

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