1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178473368, compound

HRID 1795222Notes

Reaction equation

HRID 1795222 reaction equation
C[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[CH:7][C:8]([C:12]([OH:14])=O)=[N:9]2)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:37]([O:39][C:40]([N:42]1[CH2:47][CH2:46][N:45]([C:48]([CH:50]([NH2:60])[CH2:51][CH2:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[O:49])[CH2:44][CH2:43]1)=[O:41])[CH3:38]>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[CH2:37]([O:39][C:40]([N:42]1[CH2:43][CH2:44][N:45]([C:48]([CH:50]([NH:60][C:12]([C:8]2[CH:7]=[C:6]([OH:15])[C:5]3[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=3)[N:9]=2)=[O:14])[CH2:51][CH2:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[O:49])[CH2:46][CH2:47]1)=[O:41])[CH3:38]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 220174794-Ethoxycarbonyl-1-(1-amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazineHCID 178418698HCID 178418698, compound

Product 1

HCID 178473368HCID 178473368, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a suspension of 7-methyl-4-hydroxy-2-carboxyquinoline (0.81 g, 4 mmol) in methylene chloride:DMF (4:1, 25 mL) was added 1-hydoxybenzotriazole (HOBT) (0.64 g, 4.8 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (1.09 g, 4.8 mmol) and the reaction mixture was stirred for 10 minutes. A solution of 4-ethoxycarbonyl-1-(1-amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazine (1.37 g, 4 mmol) in methylene chloride (10 mL) was added to the reaction mixture and the resulting mixture was stirred at ambient temperature for 6 hours. The solvent was evaporated in vacuo and the resulting residue was partitioned in ethyl acetate and water. The organic layers were combined and washed with water, brine and concentrated to afford an off-white foam, 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-3-(1,1-dimethylethoxycarbonyl)propyl]aminocarbonyl-4-hydroxyquinoline; (1.44 g, 68%).

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 6 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe resulting residue was partitioned in ethyl acetate
  4. washwashed with water, brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b87e1640cba94a6fa9b5bbdc1530d7e1
Source dataset
uspto-grants-2006_04
Patent number
US07026323B2

Reaction notes

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