3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 18358000, compound

HRID 849583Notes

Reaction equation

HRID 849583 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2C(=O)[C:18]3[C:13](=[CH:14]C=[CH:16][CH:17]=3)[C:12]2=[O:21])[S:2]1.Cl.C(Cl)(=O)C1C=CC=[N:26]C=1>C1(C)C=CC=CC=1.CO.C(N)CCC.O1CCCC1.C(N(CC)CC)C>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[N:26][CH:14]=2)[S:2]1

Participants

8

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 183579972-[5-(1,2-Dithiolan-3-yl)pentyl]isoindole-1,3-dione

Product 1

HCID 18358000HCID 18358000, compoundYield 32.9%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8007ButylamineSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

The reaction was carried out as described in Example 100, but using 3 ml of a solution of 1.6 mmol of 2-[5-(1,2-dithiolan-3-yl)pentyl]isoindoline-1,3-dione (prepared as described in Example 58) in toluene, 2 ml of methanol, 2 ml of butylamine, 5 ml of anhydrous tetrahydrofuran, 0.33 ml of triethylamine and 427 mg of nicotinoyl chloride hydrochloride. The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 3:1 and 1:0 by volume mixtures of ethyl acetate and hexane and a 20:1 by volume mixture of ethyl acetate and methanol as the eluent. The solvent was removed from the eluate by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 156 mg of the title compound as a yellow amorphous substance, melting at 41 to 44° C.

Workup

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  7. additiona 20:1 by volume mixture of ethyl acetate and methanol as the eluent
  8. customThe solvent was removed from the
  9. customeluate by evaporation under reduced pressure
  10. dissolutionthe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-3991dce58ef047d98bbadbe5280c8f84
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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