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

HRID 374105

反応式

HRID 374105 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eeb7f51a35804c3b9b3dbd092fa9d37a
出典データセット
uspto-grants-1992_11
特許番号
US05166341

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