Cyclopropylamine → HCID 44540959、化合物

HRID 1616016ノート

反応式

HRID 1616016 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.[CH:29]1([NH2:32])[CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[CH:29]1([NH:32][C:2]2[N:7]=[C:6]([C:8]([NH:10][C:11]3[CH:19]=[C:18]([C:20]4[CH:28]=[CH:27][CH:26]=[C:25]5[C:21]=4[CH:22]=[CH:23][NH:24]5)[CH:17]=[C:16]4[C:12]=3[CH:13]=[N:14][NH:15]4)=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:31][CH2:30]1

参加物

6

反応物 3

HCID 69828Cyclopropylamine4 回HCID 81531Diisopropylethylamine2 回HCID 44540963HCID 44540963、化合物

生成物 1

HCID 44540959HCID 44540959、化合物収率 1.8%

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). Cyclopropylamine (0.018 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 cyclopropylamine (0.018 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, cyclopropylamine (0.018 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time, cyclopropylamine (0.018 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. 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 (1.9 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. customThe crude reaction mixture
  6. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  7. customThe sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um)
  8. customProduct-containing fractions were dried under a stream of nitrogen

出典と根拠

ORDレコード
ord-fe33e8b639e947729a0171e8ab668df8
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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