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Dimethylformamide → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-phenylpyrrolidine-3-carboxamide

HRID 58692
ノート
印刷プレビュー

反応式

HRID 58692 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].CN(C(ON1N=N[C:25]2[CH:26]=CC=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:39]([N:42]([CH2:46][CH3:47])[CH:43]([CH3:45])[CH3:44])([CH3:41])C.CN([CH:51]=[O:52])C>>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:51]([CH:47]1[CH2:41][CH2:39][N:42]([C:43]2[CH:44]=[CH:26][CH:25]=[CH:24][CH:45]=2)[CH2:46]1)=[O:52]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 66832116N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1-phenylpyrrolidine-3-carboxamide収率 18%

実験手順

A mixture of the intermediate 60 (1-(4-cyanophenyl)-2-oxopyrrolidine-3-carboxylic acid) (0.124 g, 0.649 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.150 g; 0.649 mmol), HATU (0.271 g; 0.713 mmol) and N,N-diisopropylethylamine (0.280 mL; 1.62 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate and the organic layer was successively washed with sodium carbonate, brine, dried and evaporated to dryness. The crude mixture was purified by crystallization from a mixture of dichloromethane and methanol to afford 0.044 g (18%) of the desired compound as a white solid.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate
  2. washthe organic layer was successively washed with sodium carbonate, brine
  3. customdried
  4. customevaporated to dryness
  5. customThe crude mixture was purified by crystallization from a mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-e5f2621262414921a9457fa50b470017
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434722B2

反応ノート

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