Ethyl Acetate → HCID 57432613, compound

HRID 1392765Notes

Reaction equation

HRID 1392765 reaction equation
[ClH:1].CNC.[OH2:5].O[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2N=N1.Cl.[CH3:17][N:18]([CH3:27])[CH2:19][CH2:20][CH2:21]N=C=NCC.[C:28]([O:31][CH2:32][CH3:33])(=[O:30])C>CN(C)C=O>[Cl:1][C:14]1[CH:15]=[C:10]2[C:11](=[CH:12][CH:13]=1)[NH:7][C:21]([C:28]([O:31][CH2:32][CH3:33])=[O:30])=[C:20]2[C:19]([N:18]([CH3:17])[CH3:27])=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 57432613HCID 57432613, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (0.7 g) obtained in Referential Example 287 was dissolved in N,N-dimethylformamide (10 ml), and dimethylamine hydrochloride (0.26 g), 1-hydroxy-benzotriazole monohydrate (0.43 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.0 g) were added to stir the mixture at room temperature for 2 days. After the reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride in that order, the resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and hexane to obtain the title compound (0.6 g).

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride in that order, the resultant organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was recrystallized from a mixed solvent of isopropyl ether and hexane

Sources & evidence

ORD record
ord-7e0a8723dda64b9d9f39d90798c8abf8
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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