Sodium Bicarbonate → N-[4-[4-(3-methylphenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide

HRID 1268740노트

반응식

HRID 1268740 반응식
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)=O.[CH3:28][N:29]1[CH2:34][CH2:33][CH:32]([C:35](=[S:37])[NH2:36])[CH2:31][CH2:30]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:12][C:8]1[CH:7]=[C:6]([C:4]2[N:36]=[C:35]([CH:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)[S:37][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)[CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 155845011-Methylpiperidine-4-CarbothioamideHCID 18446669N-[4-[1-bromo-2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide hydrobromide

생성물 1

HCID 18446686N-[4-[4-(3-methylphenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide수율 47%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-[4-[1-bromo-2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide hydrobromide (0.60 g, 1.2 mmol) and 1-methylpiperidine-4-carbothioamide (0.19 g, 1.18 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. The residue was purified by column chromatography (packing: Chromatorex NH DM1020 (product name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=2:1) and the resulting crystals were recrystallized from ethyl acetate to give the title compound (0.26 g, yield 46%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (packing: Chromatorex NH DM1020 (product name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=2:1)
  6. customthe resulting crystals were recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-be21d7ab60f44e23bcda25f6aa1166ba
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199124B2

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