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Diisopropylethylamine → HCID 178433037、化合物

HRID 244730
ノート
印刷プレビュー

反応式

HRID 244730 の反応式
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:43][C:44]1[C:52]2[C:51]([NH2:53])=[CH:50][C:49]([C:54]3[CH:62]=[CH:61][CH:60]=[C:59]4[C:55]=3[CH:56]=[CH:57][NH:58]4)=[CH:48][C:47]=2[NH:46][N:45]=1>CN(C=O)C.C(Cl)(Cl)Cl>[F:43][C:44]1[C:52]2[C:47](=[CH:48][C:49]([C:54]3[CH:62]=[CH:61][CH:60]=[C:59]4[C:55]=3[CH:56]=[CH:57][NH:58]4)=[CH:50][C:51]=2[NH:53][C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)=[O:9])[NH:46][N:45]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 2847282-Methyl-1,3-thiazole-4-carboxylic acid2 回HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2 回HCID 178507273HCID 178507273、化合物

生成物 1

HCID 178433037HCID 178433037、化合物収率 10.7%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
20 °C

実験手順

To 2-methyl-1,3-thiazole-4-carboxylic acid (24 mg) in DMF (0.375 ml) was added HATU (69 mg) followed by DIPEA (0.043 ml), and the solution stirred for 10 min at 20° C. To this was then added a solution of 3-fluoro-6-(1H-indol-4-yl)-1H-indazol-4-amine (67 mg) in DMF (0.375 ml) and the top was placed on the vial which had been pierced with a needle. The solution was stirred at 20° C. for 73 h, heated at 50° C. for 3 h, then left to stand for 3.5 days. A further portion of 2-methyl-1,3-thiazole-4-carboxylic acid (0.024 g) in DMF (0.375 ml) was treated with HATU (0.069 g) followed by DIPEA (0.043 ml). This solution was stirred for 15 min at 20° C. then added to the original reaction mixture. This was then stirred at 20° C. for a further 72 h then loaded onto a dried aminopropyl SPE cartridge (1 g) which had been preconditioned with chloroform. The material was left on the cartridge for 2 h, then the cartridge was eluted with methanol (3 column volumes) and the solvent blown off. This was purified directly by mass directed preparative HPLC (Method A). The residue was azeotroped with methanol (5 ml) to give the title compound (7 mg) as a beige solid.

後処理

  1. stirringThe solution was stirred at 20° C. for 73 h
  2. temperatureheated at 50° C. for 3 h
  3. waitleft
  4. waitto stand for 3.5 days
  5. stirringThis solution was stirred for 15 min at 20° C.
  6. additionthen added to the original reaction mixture
  7. stirringThis was then stirred at 20° C. for a further 72 h
  8. waitThe material was left on the cartridge for 2 h
  9. washthe cartridge was eluted with methanol (3 column volumes)
  10. customThis was purified directly by mass
  11. customThe residue was azeotroped with methanol (5 ml)

出典と根拠

ORDレコード
ord-6fc31eb79ff441058a51713b4ae8bdf9
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658635B2

反応ノート

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