Triethylamine → HCID 89691090, compound

HRID 2202966Notes

Reaction equation

HRID 2202966 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:10][C:9]2=[O:23])=[CH:4][C:3]=1[NH:24][CH3:25].[CH:26]12[CH2:31][CH:30]1[C:29](=O)[O:28][C:27]2=[O:33].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C1COCC1.CC(O)=O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[C:29]([CH:30]5[CH2:31][CH:26]5[C:27]([OH:28])=[O:33])[N:24]([CH3:25])[C:3]=4[CH:4]=3)[C:9](=[O:23])[CH:10]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 896902584-(4-Chlorobenzyloxy)-1-(4-amino-3-(methylamino)phenyl)pyridin-2(1h)-one

Product 1

HCID 89691090HCID 89691090, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (2.0 g), 3-oxabicyclo[3.1.0]hexane-2,4-dione (0.662 g) and triethylamine (1.175 ml) in THF (80 ml) was stirred at room temperature overnight. After concentration of the mixture in vacuo, AcOH (80 ml) was added to the residue. The mixture was stirred at 80° C. for 1 h. After concentration of the mixture in vacuo, the mixture was neutralized with saturated NaHCO3 solution at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting solid was washed with IPE and dried to give the title compound (1.67 g) as a brown solid.

Workup

  1. stirringThe mixture was stirred at 80° C. for 1 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe resulting solid was washed with IPE
  8. customdried

Sources & evidence

ORD record
ord-e27274a416e34cefbd3cb29c3cd85c61
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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