Reaction #155504

Reaction equation

compound

2,2′-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetic acid

(tetrahydro-2H-pyran-4-yl)methanamine

HOBT

EDC.HCl

N-ethyl morpholine

→

product

Yield 49.2%

2,2′-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)bis(N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide)

Yield 49.2%

Solvents

DMF

Conditions

Workup

1. 1
   Otherreaction mixture
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice cold water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   ExtractionThe combined ethyl acetate extract
5. 5
   Washwas washed with water & brine
6. 6
   Dryingdried over sodium sulphate
7. 7
   Otherevaporated under reduced pressure
8. 8
   OtherThe crude product was triturated with hexane

Procedure

To a solution of compound prepared in example 6 (250 mg, 0.60 mmoles) in DMF (2 mL), (tetrahydro-2H-pyran-4-yl)methanamine (138 mg, 1.20 mmoles), HOBT (121 mg, 0.90 mmoles), EDC.HCl (138 mg, 0.72 mmoles) and N-ethyl morpholine (227 μL, 1.80 mmoles) were added and reaction mixture was srirred at 25° C. for 2-5 hours under nitrogen atmosphere. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was triturated with hexane to yield 180 mg (49%) of product as white solid.

Source