Ethyl Acetate → HCID 57432613, compound

HRID 2104398Notes

Reaction equation

HRID 2104398 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>[CH2:32]([O:31][C:28]([C:21]1[NH:7][C:11]2[C:10]([C:20]=1[C:19]([N:18]([CH3:17])[CH3:27])=[O:5])=[CH:15][C:14]([Cl:1])=[CH:13][CH:12]=2)=[O:30])[CH3:33]

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 obtained in Referential Example 287 (0.7 g) was dissolved in N,N-dimethylformamide (10 mL), and to the solution were added dimethylamine hydrochloride (0.26 g), 1-hydroxybenzotriazole monohydrate (0.43 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.0 g), followed by stirring at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate, and the diluted mixture was sequentially washed with 1N aqueous HCl, saturated aqueous sodium hydrogencarbonate, and saturated brine. The organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was recrystallized from a solvent mixture comprising isopropyl ether and hexane, to thereby give the title compound (0.6 g).

Workup

  1. washthe diluted mixture was sequentially washed with 1N aqueous HCl, saturated aqueous sodium hydrogencarbonate, and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue was recrystallized from a solvent mixture

Sources & evidence

ORD record
ord-da088397d1df49c5b6b27ac5f467da1d
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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