1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21088439, compound

HRID 350757Notes

Reaction equation

HRID 350757 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:18]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]3)[O:11][C:12]=2[CH2:13][CH2:14][C:15](O)=[O:16])=[CH:4][CH:3]=1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:46][N:47]1[CH2:52][CH2:51][CH:50]([CH2:53][N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:49][CH2:48]1>O.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:18]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]3)[O:11][C:12]=2[CH2:13][CH2:14][C:15]([N:57]2[CH2:56][CH2:55][N:54]([CH2:53][CH:50]3[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]3)[CH2:59][CH2:58]2)=[O:16])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 21088628HCID 21088628, compound

Product 1

HCID 21088439HCID 21088439, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[4-(4-chlorophenyl)-2-(3,5-dimethyl-1H-pyrazol-1-yl)-5-oxazolyl]propionic acid (51.5 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (41 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (46 mg), 4-[(1-methyl-4-piperidinyl)methyl]piperazine (60 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was concentrated, introduced into preparative HPLC and purified. Ethyl acetate was added to the obtained oil and the mixture was washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated to give 1-{3-[4-(4-chlorophenyl)-2-(3,5-dimethyl-1H-pyrazol-1-yl)-5-oxazolyl]propanoyl}-4-[(1-methyl-4-piperidinyl)methyl]piperazine (54.5 mg, yield 72%). Recrystallization from ethanol-isopropyl ether gave colorless prism crystals. melting point: 126–127° c.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified
  5. additionEthyl acetate was added to the obtained oil
  6. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate
  7. washThe ethyl acetate layer was washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2c2b0df504714b5fb167bcb6182d436e
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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