1-Hydroxybenzotriazole → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide

HRID 1665651ノート

反応式

HRID 1665651 の反応式
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:26]2[N:31]=[CH:30][C:29]([NH:32][C:33](=[O:38])[CH2:34][C:35]([OH:37])=O)=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.Cl.[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60]>CN(C=O)C.O>[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[C:59]([N:61]1[CH2:62][CH2:63][N:64]([C:35](=[O:37])[CH2:34][C:33]([NH:32][C:29]2[CH:30]=[N:31][C:26]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:27][CH:28]=2)=[O:38])[CH2:65][CH2:66]1)=[O:60]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874490N-(6-phenyl-pyridin-3-yl)-malonamic acidHCID 66625832(2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochloride

生成物 1

HCID 442314473-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide収率 46.1%

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 (41 mg, 0.3 mmol) and DIEA (98 mg, 0.76 mmol) were added to a stirred solution of N-(6-phenyl-pyridin-3-yl)-malonamic acid (65 mg, 0.25 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (58 mg, 0.3 mmol) followed by (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (93 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 to afford 58.5 mg (46%) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide. LCMS: 507.1 (M+1)+ 98.54%, 1H NMR: (DMSO-d6): δ 10.5 (d, 1H), 8.8 (dd, 1H), 8.2-7.86 (m, 4H), 7.5 (d, 1H), 7.34 (m, 6H), 3.8-3.4 (m, 8H), 3.2-3.1 (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

出典と根拠

ORDレコード
ord-a139505b54de4929bc172bb427e27e58
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

読み込み中…