Ammonia → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-propyl-3-phenylpropanamide
Reaction equation
FC1C=CC(N2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]([CH2:22][CH2:23][CH3:24])[C:19]([OH:21])=O)=[CH:14][CH:15]=3)C=N2)=CC=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]2C3C(=CC(C(C4C=CC=CC=4)C(C)(C)CN)=CC=3)[CH:40]=[N:39]2)=[CH:34][CH:33]=1.FC1C=CC([N:66]2C3C(=CC(C(C4C=CC=CC=4)C(CCC)C(F)=O)=CC=3)C=N2)=CC=1.N>C1COCC1.O>[F:31][C:32]1[CH:33]=[CH:34][C:35]([N:38]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]([CH2:22][CH2:23][CH3:24])[C:19]([NH2:66])=[O:21])=[CH:14][CH:15]=3)[CH:40]=[N:39]2)=[CH:36][CH:37]=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)pentanoic acid (50, mg, 0.124 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-propyl-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-propyl-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-61b8de496ff8456394e3b576c89ac3f3
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198311B2
Reaction notes
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