4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine → 5-amino-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-(morpholinomethyl)phenyl)thiazole-4-carboxamide
Reaction equation
Br[C:2]1[S:3][C:4]([NH:16]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:15])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[N:6]=1.B1([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH:34]=2)OC(C)(C)C(C)(C)O1>>[NH2:16][C:4]1[S:3][C:2]([C:37]2[CH:38]=[CH:33][CH:34]=[C:35]([CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH:36]=2)=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=1)=[O:15]Participants
3
Procedure
Following Example 278, Suzuki coupling of tert-butyl 2-bromo-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate and 3-(4-morpholinomethyl)phenylboronic acid pinacol ester gave 356 as an off-white solid (31 mg, 36% over two steps). 1H NMR (400 MHz, d6-DMSO) δ 9.80 (s, 1H), 7.98 (s, 1H), 7.80-7.73 (m, 2H), 7.65 (s, 1H), 7.49-7.38 (m, 3H), 7.35 (d, J=7.6 Hz, 1H), 3.82 (s, 3H), 3.60 (t, J=4.5 Hz, 4H), 3.53 (s, 2H), 2.45-2.33 (m, 4H). LCMS (ES+) m/z 399 (M+1)
Sources & evidence
- ORD record
- ord-1314a16cdc08440aa7f93e7115002e0c
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669361B2
Reaction notes
Loading…