Triethylamine → HCID 68662189, compound

HRID 1260869Notes

Reaction equation

HRID 1260869 reaction equation
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][NH2:21].C(N(CC)CC)C>C(O)C>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:21]([CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([O:16][CH3:15])[CH:18]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 211563-MethoxybenzylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamide

Product 1

HCID 68662189HCID 68662189, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.5 g) in ethanol (5 ml) was added a solution (3 ml) of 3-methoxybenzylamine (410 μl) and triethylamine (450 μl) in ethanol at 0° C., and the mixture was stirred at room temperature for 24 hr. The reaction solvent was evaporated under reduced pressure, and the residue was purified by preparative HPLC. 4N Hydrochloric acid-ethyl acetate solution (1 ml) was added to the obtained yellow oil at room temperature, and the precipitated crystals were filtered and recrystallized to give the title compound (110 mg).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. customthe residue was purified by preparative HPLC
  3. addition4N Hydrochloric acid-ethyl acetate solution (1 ml) was added to the obtained yellow oil at room temperature
  4. filtrationthe precipitated crystals were filtered
  5. customrecrystallized

Sources & evidence

ORD record
ord-3d09d259a15a4988a1507a01f6baa3ee
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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