5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → 4-{[4'-(2-Aminopyrimidin-5-yl)-3'-fluoro-4-(trifluoromethyl)biphenyl-2-yl]sulfonyl}piperazin-2-one
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH2:16]1)(=[O:14])=[O:13].[F:22][C:23]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[CH:25][C:24]=1[C:38]1[CH:39]=[N:40][C:41]([NH2:44])=[N:42][CH:43]=1>>[NH2:44][C:41]1[N:42]=[CH:43][C:38]([C:24]2[CH:25]=[CH:26][C:27]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=3[S:12]([N:15]3[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH2:16]3)(=[O:14])=[O:13])=[CH:28][C:23]=2[F:22])=[CH:39][N:40]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 4-((2-bromo-5-(trifluoromethyl)phenyl)-sulfonyl)-piperazin-2-one and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrimidin-2-amine. MS (ESI): mass calcd. for C21H17F4N5O3S, 495.10; m/z found, 496.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.70-8.61 (d, J=1.2, 2H), 8.40 (s, 1H), 8.10-8.03 (d, J=157.7, 1H), 7.71-7.64 (d, J=7.9, 1H), 7.64-7.58 (m, 1H), 7.39-7.37 (m, 1H), 7.36 (s, 1H), 3.34 (s, 2H), 3.22-3.17 (m, 2H), 3.17-3.12 (m, 2H).
Sources & evidence
- ORD record
- ord-f18284bb8e134fabac6aeaab71c2120e
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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