3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropan-1-amine → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19](O)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.FC1C=CC([N:41]2C3C(=CC(C(C4C=CC=CC=4)C(C)(C)CN)=CC=3)C=N2)=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:19]([NH2:41])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1Participants
3
Conditions
- Temperature
- -78 °C
Procedure
(c)(d) 3-(1-(4-Fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoic acid (80, 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)-2,3-diphenylpropanoyl fluoride 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)-2,3-diphenylpropan-amide.
Workup
- customA solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanoyl fluoride in anhydrous THF (5 mL) at −78° C. was bubbled NH3 (g) for 10 minutes
- customThe reaction mixture was sealed
- additionWater (100 mL) was added
- extractionthe reaction mixture was extracted with ethyl acetate (100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-169dcecb6415471fad0dc815d2e3fd9e
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198311B2
Reaction notes
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