Dicyclohexylcarbodiimide → HCID 14772798, compound

HRID 1885405Notes

Reaction equation

HRID 1885405 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([OH:14])=O)[CH2:9][S:8]2)[CH:2]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(N(CC)CC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([N:24]3[CH2:25][CH2:26][N:21]([C:16]4[N:15]=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:22][CH2:23]3)=[O:14])[CH2:9][S:8]2)[CH:2]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 887471-(2-Pyrimidinyl)piperazineHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 14772798HCID 14772798, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(3-pyridyl)thiazolidine-4-carboxylic acid 2.1 g, 1-(2-pyrimidinyl)piperazine. 2 hydrochyloride 2.2 g, triethylamine 1.8 g, 1-hydroxybenzotriazole 1.5 g and N,N-dimethylformamide 30 ml was added dicyclohexylcarbodiimide 2.0 g under cooling and the mixture was stirred overnight at room temperature. The resultant dicyclohexylurea was distilled off, ethyl acetate 100 ml and water 50 ml were added to the filtrate and the solution was basified by addition of potassium carbonate. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The organic layer and extract were combined, washed successively with water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethanol to give 0.8 g of 1-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]-4-(2-pyrimidinyl)piperazine.

Workup

  1. temperatureunder cooling
  2. distillationThe resultant dicyclohexylurea was distilled off
  3. additionethyl acetate 100 ml and water 50 ml were added to the filtrate
  4. additionthe solution was basified by addition of potassium carbonate
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted with ethyl acetate
  7. extractionThe organic layer and extract
  8. washwashed successively with water and saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a9869ca6287c4689a0a0527d3f87b6ca
Source dataset
uspto-grants-1992_09
Patent number
US05144035

Reaction notes

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