N-Phenyl-p-phenylenediamine → 3-oxo-N-(4-phenylamino-phenyl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide

HRID 1665649ノート

反応式

HRID 1665649 の反応式
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[O:20]=[C:21]([N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])[CH2:28][CH2:27]1)[CH2:22][C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.[C:56]1([NH:62][C:63]2[CH:68]=[CH:67][C:66]([NH2:69])=[CH:65][CH:64]=2)[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>CN(C=O)C.O>[O:20]=[C:21]([N:26]1[CH2:27][CH2:28][N:29]([C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])[CH2:30][CH2:31]1)[CH2:22][C:23]([NH:69][C:66]1[CH:65]=[CH:64][C:63]([NH:62][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:68][CH:67]=1)=[O:25]

参加物

8

反応物 5

HCID 7564N-Phenyl-p-phenylenediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

生成物 1

HCID 442314463-oxo-N-(4-phenylamino-phenyl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide収率 10%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

HOBt (70 mg, 0.5 mmol) and DIEA (11 mg, 0.9 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (50 mg, 0.3 mmol) in DMF (3 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (80 mg, 0.5 mmol) followed by N-phenyl-benzene-1,4-diamine (100 mg, 0.3 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (10% methanol in chloroform) to afford 15 mg (10%) of 3-oxo-N-(4-phenylamino-phenyl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 511.19 (M+1)+, 96.55%, 1H NMR: (CDCl3): δ 7.7 (m, 1H), 7.6 (m, 2H), 7.4 (m, 4H), 7.1 (m, 1H), 7.0 (m, 3H), 6.8 (m, 1H), 4.0 (m, 2H), 3.8 (m, 2H), 3.4 (m, 3H), 3.2 (m, 2H).

後処理

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-97c25c57632646319961b0e77e09a495
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

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