1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86650785, compound

HRID 1893579Notes

Reaction equation

HRID 1893579 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:28])=[C:7]([N:9]([CH2:14][C:15]([N:17]([N:19]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)[CH3:18])=[O:16])[CH2:10]C(O)=O)[CH:8]=1)#[N:2].CC1[C:38]2[C:33](=CC(N)=C(C)C=2)[N:32]([CH:41]2CCCC[O:42]2)N=1.O[N:48]1[C:52]2[CH:53]=CC=C[C:51]=2N=N1.CCN=C=N[CH2:62][CH2:63][CH2:64]N(C)C.[C:68]([O:71]CC)(=[O:70])C.[CH3:74]CCCCC>ClCCl.CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:28])=[C:7]([N:9]([CH2:14][C:15]([N:17]([N:19]2[CH2:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:27]2)[CH3:18])=[O:16])[CH2:10][C:41]([NH:32][CH2:33][CH2:38][N:48]([C:68]([O:71][C:63]([CH3:64])([CH3:74])[CH3:62])=[O:70])[CH:52]([CH3:51])[CH3:53])=[O:42])[CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21226206Ethyl acetate hexaneHCID 66881030HCID 66881030, compoundHCID 66882037HCID 66882037, compound

Product 1

HCID 86650785HCID 86650785, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (2.32 g, 6.13 mmol) obtained in step A, the compound of Reference Example 3 (1.67 g, 8.26 mmol) and 1-hydroxybenzotriazole (1.19 g, 8.81 mmol) were dissolved in an N,N-dimethylformamide (3 ml)-dichloromethane (40 ml) mixed solvent, WSC (1.80 g, 9.39 mmol) was added under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with an ethyl acetate-hexane=1:1 (250 ml) mixed solvent, washed with water, 10% aqueous citric acid solution, diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was washed with a diethyl ether-hexane=1:1 mixed solvent, and dried under reduced pressure to give the title compound (2.81 g, yield 81%) as a colorless solid.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionmixed solvent
  4. washwashed with water, 10% aqueous citric acid solution, diluted aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure
  8. washThe obtained solid was washed with a diethyl ether-hexane=1:1 mixed solvent
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc386c7d1441483bacda2b09bbd278a1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

Loading…