3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole → 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol
Reaction equation
C1(C(=[N:14][CH:15]([CH2:21]CC2C=C3C(=CC=2)C2=NOC(C4C(C(F)(F)F)=C(C5C=CC=CC=5)ON=4)=C2CC3)[C:16](OCC)=[O:17])C2C=CC=CC=2)C=CC=CC=1.[C:51]1([N:57]2[C:61]([C:62]([F:65])([F:64])[F:63])=[C:60]([C:66]3[O:70][N:69]=[C:68]4[C:71]5[C:76]([CH2:77][CH2:78][C:67]=34)=[CH:75][C:74]([CH:79]=[CH2:80])=[CH:73][CH:72]=5)[CH:59]=[N:58]2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>>[NH2:14][C:15]([CH3:21])([CH2:80][CH2:79][C:74]1[CH:75]=[C:76]2[C:71](=[CH:72][CH:73]=1)[C:68]1=[N:69][O:70][C:66]([C:60]3[CH:59]=[N:58][N:57]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:61]=3[C:62]([F:63])([F:64])[F:65])=[C:67]1[CH2:78][CH2:77]2)[CH2:16][OH:17]Participants
3
Reactant 2
Product 1
Procedure
The titled compound was prepared using the experimental protocols described for Preparation 91A, and Example 93 employing 3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (89A) as a starting material. The compound had an HPLC retention time=3.03 min. (condition C); LC/MS M+1=483.3; 1H NMR (400 MHz, MeOD) δ ppm 8.14 (1H, s), 7.85 (1H, d, J=7.7 Hz), 7.53-7.65 (5H, m), 7.30 (1H, s), 7.28 (1H, d, J=7.9 Hz), 3.67 (1H, d, J=11.5 Hz), 3.56 (1H, d, J=11.5 Hz), 3.03 (2H, t, J=6.9 Hz), 2.90 (2H, t, J=6.9 Hz), 2.66-2.81 (2H, m), 1.86-2.07 (2H, m), 1.37 (3H, s).
Sources & evidence
- ORD record
- ord-4f64c8e07fd5453d8a5609fc74712440
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216972B2
Reaction notes
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