Ammonia → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-ethyl-3-phenylpropanamide
Reaction equation
FC1C=CC([N:8]2C3C(=CC(C(C4C=CC=CC=4)C(CC)C(O)=O)=CC=3)C=N2)=CC=1.FC1C=CC(N2C3C(=CC(C(C4C=CC=CC=4)C(C)(C)CN)=CC=3)C=N2)=CC=1.[F:58][C:59]1[CH:64]=[CH:63][C:62]([N:65]2[C:73]3[C:68](=[CH:69][C:70]([CH:74]([C:81]4[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=4)[CH:75]([CH2:79][CH3:80])[C:76](F)=[O:77])=[CH:71][CH:72]=3)[CH:67]=[N:66]2)=[CH:61][CH:60]=1.N>C1COCC1.O>[F:58][C:59]1[CH:64]=[CH:63][C:62]([N:65]2[C:73]3[C:68](=[CH:69][C:70]([CH:74]([C:81]4[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=4)[CH:75]([CH2:79][CH3:80])[C:76]([NH2:8])=[O:77])=[CH:71][CH:72]=3)[CH:67]=[N:66]2)=[CH:61][CH:60]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
(c)(d) 2-((1-(4-Fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)butanoic acid (60, mg, 0.154 mmol) was converted into the acid fluoride using the identical procedure to that for Synthetic Intermediate I above. A solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-ethyl-3-phenylpropanoyl fluoride (0.32 mmol) in anhydrous THF (5 mL) at −78° C. was bubbled NH3 (g) for 10 minutes. The reaction mixture was sealed and stirred at −78° C. for 15 min and at rt for 1 hr. Water (100 mL) was added, the reaction mixture was extracted with ethyl acetate (100 mL), dried (Na2SO4), and concentrated to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-ethyl-3-phenylpropanamide.
Workup
- customThe reaction mixture was sealed
- extractionthe reaction mixture was extracted with ethyl acetate (100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cbaf7c4db90a42519b9ff4ce4c792d87
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198311B2
Reaction notes
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