Sodium Carbonate → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramide

HRID 1927592노트

반응식

HRID 1927592 반응식
[CH2:1]([CH:3]([CH2:20][CH3:21])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:9]([F:19])[CH:8]=1)=[O:5])[CH3:2].Br[CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[NH3:6].[CH2:29]([N:26]([CH2:27][CH3:28])[C:24]([CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[CH:3]([CH2:1][CH3:2])[CH2:20][CH3:21])=[CH:8][C:9]=2[F:19])[CH2:18][CH2:17]1)=[O:25])[CH3:30]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 14897375HCID 14897375, 화합물HCID 58870794HCID 58870794, 화합물

생성물 2

HCID 222AmmoniaHCID 16666511N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramide수율 88.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide (0.030 g, 0.084 mmol), 2-bromo-N,N-diethyl-2-phenyl-acetamide (0.025 g, 0.094 mmol), and Na2CO3 (0.013 g, 0.12 mmol) in DMF (2 mL) was stirred at rt for 18 h. The reaction mixture was diluted with EtOAc (25 mL) and washed with H2O (3×15 mL). The organic layer was dried (Na2SO4) and concentrated. Chromatography of the resulting residue (SiO2; 2 M NH3 in MeOH/DCM) gave the title compound (0.018 g, 38%). MS (ESI): mass calcd. for C28H39FN4O2, 482.31. m/z found, 483.5 [M+H]+. 1H NMR (CDCl3): 7.53-7.45 (m, 3H), 7.38-7.31 (m, 3H), 7.10-7.07 (m, 1H), 6.89-6.84 (m, 1H), 3.50-3.37 (m, 2H), 3.30-3.15 (m, 2H), 3.08 (s, 4H), 2.70 (br s, 4H), 2.05-2.01 (m, 1H), 1.75-1.68 (m, 2H), 1.60-1.52 (m, 2H), 1.09-1.02 (m, 6H), 0.97-0.91 (m, 6H).

후처리

  1. washwashed with H2O (3×15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-60ee2d781f204c6abbda739939fe1448
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183239B2

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