Carbon Dioxide → HCID 23694154, compound

HRID 352928Notes

Reaction equation

HRID 352928 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1.CCCCCC.[C:18](=[O:20])=[O:19].C([Li:25])CCC>C(OCC)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:5]2[S:1][C:2]([C:18]([O-:20])=[O:19])=[N:3][CH:4]=2)[CH:7]=1.[Li+:25]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8058HexaneHCID 22709894HCID 22709894, compoundHCID 178418339Butyllithium

Product 1

HCID 23694154HCID 23694154, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(5-thiazolyl)pyridine (400 mg) in diethyl ether (15 mg), n-butyl lithium (a 1.52 N hexane solution, 1.45 ml) was added dropwise at −78° C. After stirring for 30 minutes, a carbon dioxide gas was blown into the reaction mixture. After 10 minutes, a cooling bath was removed and the temperature of the reaction mixture was allowed to rise back slowly to room temperature. The reaction mixture was concentrated, whereby the residue of lithium 5-(3-pyridyl)thiazole-2-carboxylate was obtained as a white solid. To a solution of the resulting residue in N,N-dimethylformamide (10 ml) were added 1-[(5-chloroindol-2-yl)sulfonyl]piperazine hydrochloride (600 mg), 1-hydroxybenzotriazole monohydrate (255 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (360 mg) at room temperature. After stirring for 3 days, ethyl acetate (50 ml) and water (100 ml) were added to the reaction mixture. The white precipitate thus obtained was collected by filtration and washed with water and ethyl acetate, whereby the title compound (727 mg) was obtained as a pale brown solid. A portion of the compound was added with an aqueous solution of hydrochloric acid, followed by concentration and drying. The product thus obtained showed the following data.

Workup

  1. waitAfter 10 minutes
  2. customa cooling bath was removed
  3. customto rise back slowly to room temperature
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-50af0ecfab04403c8a0c38208c06740d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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