Water → HCID 58992615, 화합물

HRID 602146

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HRID 602146 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 58992615HCID 58992615, 화합물수율 58%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 679Dimethyl Sulfoxide용매

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온도
140 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f569914275bf4e65bc69dfc738e7627e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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