Ethyl Acetate → HCID 57432613, compound

HRID 902871Notes

Reaction equation

HRID 902871 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 87 was dissolved in N,N-dimethylformamide (10 ml), and dimethylamine hydrochloride (0.26 g), 1-hydroxybenzotriazole 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-89ca36132e0d48e0ad6186e303acf691
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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