p-Toluenesulfonic acid → 5,6-bis-(4-chloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

HRID 1693505

反応式

HRID 1693505 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[C:19]1([N:25]2[C:29]([NH2:30])=[C:28]([NH2:31])[CH:27]=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:31]=[C:28]3[CH:27]=[N:26][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:29]3=[N:30][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 189461,2-Ethanedione, 1,2-bis(4-chlorophenyl)-HCID 516892Sodium BicarbonateHCID 106548192-phenyl-2H-pyrazole-3,4-diamine

生成物 1

HCID 116185645,6-bis-(4-chloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyrazine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1,2-bis-(4-chloro-phenyl)-ethane-1,2-dione from Step A (˜20 mg), 2-phenyl-2H-pyrazole-3,4-diamine from Step B (25 mg) and p-TSA in MeOH (1 mL) is heated to 80° C. for 2 h. After cooling down to room temperature, the mixture is treated with saturated aqueous NaHCO3 solution (3 mL) and extracted with EtOAc (3×2 mL). The organic layers are combined and concentrated. The residue is purified by Preparative LC/MS to provide the title compound 5,6-bis-(4-chloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyrazine. 1H NMR (CDCl3) δ(ppm) 8.51(s, 1H), 8.34 (d, 2H), 7.56(t, 2H), 7.46(d, 2H), 7.32˜7.43 (m, 7H); HPLC-MS calculated for C23H14Cl2N4 (M+H+): 417.1. Found: 417.1.

後処理

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with EtOAc (3×2 mL)
  3. concentrationconcentrated
  4. customThe residue is purified by Preparative LC/MS

出典と根拠

ORDレコード
ord-1227e6520551406cb8c2f584572f9750
出典データセット
uspto-grants-2012_04
特許番号
US08158634B2

関連ノート

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