Dimethyl Sulfoxide → HCID 58992629, 화합물

HRID 602133

반응식

HRID 602133 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH3:23])=[O:10])[CH2:2]1.F[C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28].CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[S:15][C:11]([C:9]([NH:8][CH2:7][CH:3]3[CH2:4][CH2:5][CH2:6][N:1]([C:25]4[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=4[C:27]([O:29][CH3:30])=[O:28])[CH2:2]3)=[O:10])=[C:12]([CH3:23])[N:13]=2)=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 67854Benzoic acid, 2-fluoro-, methyl esterHCID 57572157N-(Piperidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide

생성물 1

HCID 58992629HCID 58992629, 화합물수율 20.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
130 °C

실험 절차

N-(Piperidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (105 mg, 0.300 mmol) and methyl 2-fluorobenzoate (0.0382 mL, 0.300 mmol) were added to dimethylsulfoxide (5 mL). To this mixture, potassium carbonate (82.9 mg, 0.600 mmol) was added and the mixture was stirred for 6 hours at 130° C. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 29.5 mg (20%) of the desired compound as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  4. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

출처 및 근거

ORD 기록
ord-42447cb694f0415a805ff92e6cdbd23f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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