Hydrochloric Acid → 1-(4-(2'-Chloro-5-methoxy-[1,1'-biphenyl]-3-carbonyl)piperazin-1-yl)prop-2-en-1-one

HRID 588810ノート

反応式

HRID 588810 の反応式
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13]C(C)(C)C)=O)[CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].Cl.CO.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([O:37][CH3:38])[CH:36]=1)C(O)=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:30]([C:11]([N:8]2[CH2:7][CH2:6][N:5]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:10][CH2:9]2)=[O:13])[CH:29]=1

参加物

10

反応物 7

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 532258043-(2-Chlorophenyl)-5-methoxybenzoic acidHCID 58593060tert-Butyl 4-acryloylpiperazine-1-carboxylate

生成物 1

HCID 1176071631-(4-(2'-Chloro-5-methoxy-[1,1'-biphenyl]-3-carbonyl)piperazin-1-yl)prop-2-en-1-one収率 52%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-acryloylpiperazine-1-carboxylate (260 mg, 1.07 mmol) in DCM (2 mL), a solution of HCl in MeOH (10 mL, 28.6 mmol) was added and the resulting mixture was stirred at room temperature for 1 h. The mixture was concentrated in vacuo. The residue was added to the solution of 3-(2-chlorophenyl)-5-methoxybenzoic acid (280 mg, 1.07 mmol), HOBt (290 mg, 2.17 mmol), EDCI.HCl (410 mg, 2.17 mmol) and Et3N (324 mg, 3.21 mmol) in DMF (10 mL). The resulting mixture was stirred at room temperature for 16 h and partitioned between DCM and saturated NaHCO3 solution. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the desired product (200 mg, 52% yield). ESI-MS m/z: 385.2[M+H]+.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. stirringThe resulting mixture was stirred at room temperature for 16 h
  3. custompartitioned between DCM and saturated NaHCO3 solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1)

出典と根拠

ORDレコード
ord-7285c600060044cd938c36ed92417e48
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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