Water → HCID 58992615、化合物

HRID 602146

反応式

HRID 602146 の反応式
[NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH3:22])=[O:9])[CH2:2]1.F[C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[S:14][C:10]([C:8]([NH:7][CH2:6][CH:3]3[CH2:4][CH2:5][N:1]([C:24]4[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=4[C:26]([O:28][CH3:29])=[O:27])[CH2:2]3)=[O:9])=[C:11]([CH3:22])[N:12]=2)=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67854Benzoic acid, 2-fluoro-, methyl esterHCID 58992652HCID 58992652、化合物

生成物 1

HCID 58992615HCID 58992615、化合物収率 58%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
140 °C

実験手順

N-(Pyrrolidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (168 mg, 0.500 mmol) and methyl 2-fluorobenzoate (0.127 mL, 1.00 mmol) were dissolved in dimethylsulfoxide (4 mL). To this solution, potassium carbonate (138 mg, 1.00 mmol) and tetrabutylammonium iodide (18.5 mg, 0.0500 mmol) were added and the mixture was stirred at 140° C. for 6 hours. Subsequently, the reaction mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate and 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=4:1->2:1) gave 136 mg (58%) of the desired compound as a colorless amorphous product.

後処理

  1. temperatureto cool
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washthe extract washed with brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1->2:1)

出典と根拠

ORDレコード
ord-f569914275bf4e65bc69dfc738e7627e
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

関連ノート

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