Lithium Chloride → HCID 86716175, compound

HRID 1481351Notes

Reaction equation

HRID 1481351 reaction equation
COC([CH:5]1[CH2:10][C:9]([C:18]#[N:19])([C:11]2[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:8][CH2:7][C:6]1=[O:20])=O.[Li+].[Cl-]>CS(C)=O.O>[Cl:17][C:14]1[N:13]=[CH:12][C:11]([C:9]2([C:18]#[N:19])[CH2:8][CH2:7][C:6](=[O:20])[CH2:5][CH2:10]2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 89704722HCID 89704722, compound

Product 1

HCID 86716175HCID 86716175, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-cyano-5-(6-chloropyridin-3-yl)-2-oxocyclohexanecarboxylic acid methyl ester (10.6 mmol) and LiCl (21.1 mmol) in 15 mL wet DMSO was heated to 120° C. under microwave conditions for 2 h. The reaction mixture was diluted with water and extracted 3 times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc (95/5 to 20/80) gives the desired compound as yellow solid.

Workup

  1. extractionextracted 3 times with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-8178171716684403b01a52a0738cdd8e
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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