2-Bromo-N-tert-butyl-1,3-thiazole-5-carboxamide → N-tert-butyl-2-(4-((S)-1-((R)-6-(2-cyano-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)thiazole-5-carboxamide
Reaction equation
[CH3:1][C:2]([CH3:36])([CH2:5][C@@:6]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:16]=2)[CH3:14])[CH2:8][CH2:7]1)[C:3]#[N:4].Br[C:38]1[S:39][C:40]([C:43]([NH:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[CH:41][N:42]=1>>[C:46]([NH:45][C:43]([C:40]1[S:39][C:38]([C:18]2[CH:19]=[CH:20][C:15]([C@@H:13]([N:9]3[CH2:8][CH2:7][C@:6]([CH2:5][C:2]([C:3]#[N:4])([CH3:36])[CH3:1])([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[O:11][C:10]3=[O:12])[CH3:14])=[CH:16][CH:17]=2)=[N:42][CH:41]=1)=[O:44])([CH3:49])([CH3:47])[CH3:48]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 2,2-dimethyl-3-((R)-2-oxo-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanenitrile and 2-bromo-N-tert-butylthiazole-5-carboxamide following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.292 min, m/z=545.4; 1H NMR (CDCl3) 1.25 (s, 3H), 1.40 (s, 3H), 1.49 (d, 3H), 2.11 (s, 2H), 2.26 (m, 1H), 2.42 (m, 2H), 2.88 (m, 1H), 5.61 (m, 1H), 5.73 (s, 1H), 6.85 (m, 2H), 7.31 (m, 5H), 7.60 (m, 2H), 8.00 (m, 1H).