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 2265511Notes

Reaction equation

HRID 2265511 reaction equation
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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-29f7eb81ccd6436eb62f48f1ed5ca0c9
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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