Triethylamine → HCID 58992676、化合物

HRID 602138ノート

反応式

HRID 602138 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH2:15][NH:16][C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)=[O:18])=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.[CH3:25][O:26][C:27]([C:29]1[CH:30]=[C:31](OB(O)O)[CH:32]=[CH:33][CH:34]=1)=[O:28].C(N(CC)CC)C>C(OCC)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH2:15][NH:16][C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:33]4[CH:34]=[C:29]([CH:30]=[CH:31][CH:32]=4)[C:27]([O:26][CH3:25])=[O:28])[CH2:20]3)=[O:18])=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 671702873-Methoxycarbonylphenylboric acidHCID 67266868HCID 67266868、化合物

生成物 1

HCID 58992676HCID 58992676、化合物収率 13.1%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 3283Diethyl Ether溶媒

実験手順

N-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methyl]piperidine-3-carboxamide hydrochloride (123 mg, 0.318 mmol) was suspended in diethyl ether. The suspension washed sequentially with a 0.1 mol/L aqueous sodium hydroxide solution and brine and was dried over magnesium sulfate. The solvent was then evaporated and the resulting residue was dissolved in dichloromethane (10 mL). To this solution, 3-(methoxycarbonyl)phenylboric acid (114 mg, 0.636 mmol), molecular sieves 4 Å (300 mg), copper (II) acetate (122 mg, 0.636 mmol) and triethylamine (0.222 mL, 1.59 mmol) were added and the mixture was stirred at room temperature for 16 hours. Subsequently, the reaction mixture was filtered through Celite and a saturated aqueous sodium bicarbonate solution was added to the filtrate. The mixture was extracted with ethyl acetate. The extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=2:1->0:1) gave 20.1 mg (13%) of the desired compound as a colorless powder.

後処理

  1. washThe suspension washed sequentially with a 0.1 mol/L aqueous sodium hydroxide solution and brine
  2. dry with materialwas dried over magnesium sulfate
  3. customThe solvent was then evaporated
  4. dissolutionthe resulting residue was dissolved in dichloromethane (10 mL)
  5. filtrationSubsequently, the reaction mixture was filtered through Celite
  6. additiona saturated aqueous sodium bicarbonate solution was added to the filtrate
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe extract washed with brine
  9. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  10. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=2:1->0:1)

出典と根拠

ORDレコード
ord-e7bba7ff48534b64a8f8d149447f20a3
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

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