Lithium cyanide → N-[6-Chloro-2-[(3R)-3-cyano-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217905Notes

Reaction equation

HRID 2217905 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14](OS(C)(=O)=O)[CH2:13]1)[CH:6]=[CH:5]2.[C-:32]#[N:33].[Li+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@@H:14]([C:32]#[N:33])[CH2:13]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 75478Lithium cyanideHCID 86609739N-[6-Chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 68809670N-[6-Chloro-2-[(3R)-3-cyano-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method of example 96, using N-[6-chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (example 33 (a)) (0.33 g) and lithium cyanide in N,N-dimethylformamide (6 mL, 0.5M). Purification (SiO2, isohexane:ethyl acetate 60:40, as eluant) gave the sub-title compound as a solid (0.066 g).

Workup

  1. customPrepared
  2. customPurification (SiO2, isohexane:ethyl acetate 60:40, as eluant)

Sources & evidence

ORD record
ord-e6961eb50cab4ed9b4b4a78e4431c9cd
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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