3,5-Bis(trifluoromethyl)benzamide → 2-[5-(3,5-Bis-trifluoromethyl-benzoylamino)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid
Reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][CH:4]([C:8]1[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=[C:12](C(F)(F)F)[CH:13]=1)[C:5]([OH:7])=[O:6].[F:25][C:26]([F:41])([F:40])[C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:30]([NH2:32])=[O:31]>>[F:25][C:26]([F:40])([F:41])[C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:35]=1)[C:30]([NH:32][C:12]1[CH:13]=[C:8]([CH:4]([CH2:3][CH:2]([CH3:1])[CH3:24])[C:5]([OH:7])=[O:6])[CH:9]=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:26]([F:41])([F:40])[F:25])=[CH:20][CH:19]=2)[CH:11]=1)=[O:31]Participants
3
Procedure
The title compound was prepared by a Buchwald coupling reaction of 4-methyl-2-(5-trifluoromethyl-biphenyl-3-yl)pentanoic acid (intermediate compound 1g) with 3,5-bis(trifluoromethyl)-benzamide under the conditions described in Example 1; 1H NMR (400 MHz, MeOD) δ ppm 0.97 (dd, J=6.60, 2.45 Hz, 6 H), 1.56 (dt, J=13.27, 6.69 Hz, 1 H), 1.75 (ddd, J=13.88, 7.21, 7.03 Hz, 1 H), 2.02 (ddd, J=13.57, 7.70, 7.58 Hz, 1 H), 3.78 (t, J=7.70 Hz, 1 H), 7.47 (s, 1 H), 7.75-7.85 (m, 5 H), 8.08 (s, 1 H), 8.21 (s, 1 H), 8.60 (s, 2 H); Calcd for C28H22F9NO3 (M+H) 592.15, Found 592.1.
Sources & evidence
- ORD record
- ord-d62c37614eb946278115e1ba7f1c87a4
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951843B2
Reaction notes
Loading…