1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25099275, compound

HRID 2381952Notes

Reaction equation

HRID 2381952 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)CCCN=C=NCC.ON1[C:32]2[CH:33]=[CH:34][CH:35]=C[C:31]=2[N:30]=[N:29]1.NN1CCCCC1>C(Cl)Cl>[N:30]1([NH:29][C:13]([C:10]2[CH:11]=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][CH:9]=2)=[O:15])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 166581-AminopiperidineHCID 757711-HydroxybenzotriazoleHCID 7473892-Phenylpyrimidine-5-carboxylic acid

Product 1

HCID 25099275HCID 25099275, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenyl-pyrimidine-5-carboxylic acid (150 mg, 075 mmol) in DCM (10 mL) is added 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide (158 mg, 0.83 mmol) and N-hydroxybenzotriazole (112 mg, 0.83 mmol) at rt and the mixture is stirred for 10 min. 1-Aminopiperidine (150 mg, 1.5 mmol) is added. The mixture is stirred at rt overnight. The mixture is washed with 2 N aqueous HCl (5 mL), saturated aqueous NaHCO3, (5 mL), and water (5 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% EtOAc in heptane to afford 2-phenyl-pyrimidine-5-carboxylic acid piperidin-1-ylamide (125 mg) as a solid. MS: 290 (M+H).

Workup

  1. stirringThe mixture is stirred at rt overnight
  2. washThe mixture is washed with 2 N aqueous HCl (5 mL), saturated aqueous NaHCO3, (5 mL), and water (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with 10% EtOAc in heptane

Sources & evidence

ORD record
ord-1bf9d56f3d9c43a791ccf5bf92a1e9eb
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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