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

HRID 58692Notes

Reaction equation

HRID 58692 reaction equation
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]

Participants

5

Reactant 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)

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e5f2621262414921a9457fa50b470017
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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