Potassium Carbonate → N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide

HRID 69106

反応式

HRID 69106 の反応式
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([NH:8][NH2:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([NH:24][C:25](=[O:27])[CH3:26])=[C:19]([C:28](=O)/[CH:29]=[CH:30]/N(C)C)[CH:18]=1.O.C(OCC)(=O)C>C(O)C>[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([NH:24][C:25](=[O:27])[CH3:26])=[C:19]([C:28]2[N:8]([CH:5]3[CH2:6][CH2:7][O:2][CH2:3][CH2:4]3)[N:9]=[CH:30][CH:29]=2)[CH:18]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 17773358(Oxan-4-yl)hydrazine hydrochlorideHCID 22728543Water ethylacetateHCID 86694309N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide

生成物 1

HCID 66696267N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide収率 56.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 3.37 g of tetrahydro-2H-pyran-4-ylhydrazine hydrochloride in 120 mL of ethanol was added 3.82 g of powdery potassium carbonate, followed by stirring at room temperature for 30 minutes. To a mixture was added 6 g of N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide, followed by stirring at 80° C. for 16 hours and cooling to room temperature. The mixture was poured into a mixture of water/ethyl acetate, and the aqueous layer was separated. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 3.96 g of N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide.

後処理

  1. stirringby stirring at 80° C. for 16 hours
  2. temperaturecooling to room temperature
  3. customthe aqueous layer was separated
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-47f6aa8a15494a88af32a108a5e08c8f
出典データセット
uspto-grants-2014_09
特許番号
US08822448B2

関連ノート

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