Trifluoroacetic acid → 3-{4-[(3-Aminopropyl)amino]-1,2,5-oxadiazol-3-yl}-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one trifluoroacetate
Reaction equation
C1([C:7](=[N:14]CCCO)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:52][C:53]1[CH:54]=[C:55]([N:60]2[C:64](=[O:65])[O:63][N:62]=[C:61]2[C:66]2[C:67]([NH:71][C:72](=O)[C:73](F)(F)F)=[N:68][O:69][N:70]=2)[CH:56]=[CH:57][C:58]=1[F:59].[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81]>O1CCCC1>[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81].[NH2:14][CH2:7][CH2:73][CH2:72][NH:71][C:67]1[C:66]([C:61]2[N:60]([C:55]3[CH:56]=[CH:57][C:58]([F:59])=[C:53]([Cl:52])[CH:54]=3)[C:64](=[O:65])[O:63][N:62]=2)=[N:70][O:69][N:68]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3-[(diphenylmethylene)amino]propan-1-ol (80 mg, 0.33 mmol) and triphenylphosphine (93 mg, 0.36 mmol) in tetrahydrofuran (1 mL) at 0° C. was treated with diisopropyl azodicarboxylate (75 μL, 0.38 mmol) dropwise. The reaction mixture was stirred at 0° C. for 15 min, treated with a solution of N-{4-[4-(3-chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-2,2,2-trifluoroacetamide (100 mg, 0.25 mmol) in tetrahydrofuran (0.5 mL), and stirred at 25° C. for 16 h. The reaction mixture was treated with trifluoroacetic acid (1 mL), stirred at 25° C. for 3 h, and concentrated to a crude residue. This material was purified by preparative LCMS to give the desired product (18 mg, 15%). LCMS for C13H13ClFN6O3 (M+H)+: m/z=355.1
Workup
- stirringstirred at 25° C. for 16 h
- stirringstirred at 25° C. for 3 h
- concentrationconcentrated to a crude residue
- customThis material was purified by preparative LCMS
Sources & evidence
- ORD record
- ord-adb210acb43242009ba43aaed9c5dbd7
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822511B2
Reaction notes
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