1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21088430, compound

HRID 350758Notes

Reaction equation

HRID 350758 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[S:23]([CH3:26])(=[O:25])=[O:24])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][CH:3]=1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:48][N:49]1[CH2:54][CH2:53][CH:52]([CH2:55][N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)[CH2:51][CH2:50]1>O.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[S:23]([CH3:26])(=[O:25])=[O:24])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([N:59]2[CH2:58][CH2:57][N:56]([CH2:55][CH:52]3[CH2:53][CH2:54][N:49]([CH3:48])[CH2:50][CH2:51]3)[CH2:61][CH2:60]2)=[O:17])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 230617453-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionic acid

Product 1

HCID 21088430HCID 21088430, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propionic acid (50 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 the mixture was 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. A 4N hydrochloric acid ethyl acetate solution was added to the ethyl acetate layer and the mixture was concentrated to give 1-(3-{4-(4-chlorophenyl)-2-[2-(methylsulfonyl)-1H-imidazol-1-yl]-5-oxazolyl}propanoyl)-4-[(1-methyl-4-piperidinyl)methyl]piperazine 3 hydrochloric acid (65.0 mg, yield 66%).

Workup

  1. extractionthe mixture was extracted 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. additionA 4N hydrochloric acid ethyl acetate solution was added to the ethyl acetate layer
  8. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-c5eb8f3e481d4a0695484be62ad9ff06
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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