Ethylamine → HCID 44541048、化合物

HRID 1616014ノート

反応式

HRID 1616014 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH2:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[CH2:29]([NH:31][C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1)[CH3:30]

参加物

6

反応物 3

HCID 6341Ethylamine5 回HCID 81531Diisopropylethylamine3 回HCID 44540963HCID 44540963、化合物

生成物 1

HCID 44541048HCID 44541048、化合物収率 3.2%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 22036561Dimethyl sulfoxide methanol溶媒

反応条件

温度
160 °C

実験手順

To a microwave vial was added 2 ml of a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (350 mg, 0.90 mmol, prepared as described in Example 18) in DMSO (14 ml). Ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Further ethylamine (0.021 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, ethylamine (0.021 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were both added to the mixture and it was heated at 160° C. for 2 h under microwave irradiation. Finally, additional ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 170° C. for 1 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method E). The sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (3.3 mg).

後処理

  1. temperaturethe mixture was heated at 160° C. for 2 h under microwave irradiation
  2. temperaturethe mixture was heated at 160° C. for 1 h under microwave irradiation
  3. additionboth added to the mixture and it
  4. temperaturewas heated at 160° C. for 2 h under microwave irradiation
  5. temperaturethe mixture was heated at 170° C. for 1 h under microwave irradiation
  6. customThe crude reaction mixture
  7. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  8. customThe sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um)
  9. customProduct-containing fractions were dried under a stream of nitrogen

出典と根拠

ORDレコード
ord-7958c17424ac4c3aaf167016e588e3d7
出典データセット
uspto-grants-2014_07
特許番号
US08765743B2

反応ノート

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