Phenol → 1-(4-Aminocinnolin-7-ylmethyl)-4-[2-(5-chlorothiophen-2-yl)-ethenesulfonyl]-piperazin-2-one

HRID 1432996ノート

反応式

HRID 1432996 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH:22]=[CH:23][C:24]4[S:25][C:26]([Cl:29])=[CH:27][CH:28]=4)(=[O:21])=[O:20])[CH2:15][C:14]3=[O:30])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.C1(O)C=CC=CC=1.C([O-])(=O)C.[NH4+:42]>C(OCC)(=O)C>[NH2:42][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH:22]=[CH:23][C:24]4[S:25][C:26]([Cl:29])=[CH:27][CH:28]=4)(=[O:20])=[O:21])[CH2:15][C:14]3=[O:30])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 996PhenolHCID 517165Ammonium AcetateHCID 541340031-(4-Chlorocinnolin-7-ylmethyl)-4-[2-(5-chlorothiophen-2-yl)-ethenesulfonyl]-piperazin-2-one

生成物 1

HCID 543207671-(4-Aminocinnolin-7-ylmethyl)-4-[2-(5-chlorothiophen-2-yl)-ethenesulfonyl]-piperazin-2-one収率 35.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

1-(4-Chlorocinnolin-7-ylmethyl)-4-[2-(5-chlorothiophen-2-yl)-ethenesulfonyl]-piperazin-2-one (0.06 g, 0.12 mmol) is treated with phenol (0.20 g) and ammonium acetate (0.2 g, 2.6 mmol) and heated to 120° C. for 45 minutes. The reaction mixture is cooled, diluted with ethyl acetate and washed with 1 N NaOH (3×100 mL) and water. The organic layer is concentrated and the residue is purified by reverse phase HPLC (20% aqueous TFA (0.1%)/acetonitrile to 100% acetonitrile). Fractions containing the desired product are lyophilized to obtain the title compound (0.02 g, 0.043 mmol). MS m/z: [M+H]+=464; 1H NMR (CD3OD, 300 MHz) δ8.6 (s, 1H), 8.4 (d, 1H), 7.75 (d, 1H), 7.65 (d, 1H), 7.35 (d, 1H), 7.1 (d, 1H), 6.8 (d, 1H), 4.9 (s, 2H), 4.05 (s, 2H), 3.6 (m, 4H).

後処理

  1. temperatureThe reaction mixture is cooled
  2. washwashed with 1 N NaOH (3×100 mL) and water
  3. concentrationThe organic layer is concentrated
  4. customthe residue is purified by reverse phase HPLC (20% aqueous TFA (0.1%)/acetonitrile to 100% acetonitrile)
  5. additionFractions containing the desired product

出典と根拠

ORDレコード
ord-2aca009ef11c496cbbacc5ae4fd799a7
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

読み込み中…