Sodium Hydroxide → N-(6-isopropylpyridin-3-yl)-N-({1-[(4-methylpyridin-2-yl)methyl]pyrazol-4-yl}methyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide

HRID 218740

反応式

HRID 218740 の反応式
Cl.[CH:2]([C:5]1[N:10]=[CH:9][C:8]([N:11]([CH2:24][C:25]2[CH:26]=[N:27][NH:28][CH:29]=2)[C:12]([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].Cl.Cl[CH2:32][C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][N:34]=1.[OH-].[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH:2]([C:5]1[N:10]=[CH:9][C:8]([N:11]([CH2:24][C:25]2[CH:26]=[N:27][N:28]([CH2:32][C:33]3[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][N:34]=3)[CH:29]=2)[C:12]([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 200610712-(Chloromethyl)-4-methylpyridine hydrochlorideHCID 67183012N-(6-isopropylpyridin-3-yl)-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride

生成物 1

HCID 59597447N-(6-isopropylpyridin-3-yl)-N-({1-[(4-methylpyridin-2-yl)methyl]pyrazol-4-yl}methyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-(6-isopropylpyridin-3-yl)-N-[(pyrazol-4-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride (0.99 g) in methylene chloride (10 mL) were added tetra-n-butylammonium hydrogensulfate (0.82 g), 2-chloromethyl-4-methylpyridine hydrochloride (0.86 gland 1 mol/L-aqueous sodium hydroxide solution (24.0 mL). The mixture was stirred at room temperature for one day. The reaction mixture was partitioned between water and chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-(6-isopropylpyridin-3-yl)-N-({1-[(4-methylpyridin-2-yl)methyl]pyrazol-4-yl}methyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide. This compound was dissolved in ethyl acetate, and 4 mol/L-HCl/dioxane (2.4 mL) was added. The precipitated solid was collected by filtration to give N-(6-isopropylpyridin-3-yl)-N-({1-[(4-methylpyridin-2-yl)methyl]pyrazol-4-yl}methyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide dihydrochloride (0.61 g).

後処理

  1. customThe reaction mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-c9b320effa2d47718266512a93b8fd1b
出典データセット
uspto-grants-2012_06
特許番号
US08198454B2

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