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

HRID 1927592ノート

反応式

HRID 1927592 の反応式
[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]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 14897375HCID 14897375、化合物HCID 58870794HCID 58870794、化合物

生成物 2

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-60ee2d781f204c6abbda739939fe1448
出典データセット
uspto-grants-2012_05
特許番号
US08183239B2

反応ノート

読み込み中…