tert-Butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate → 5-Amino-N-(1-Methyl-1H-Pyrazol-4-Yl)-2-(3-(Piperazin-1-yl)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.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[C:34]([N:38]3[CH2:43][CH2:42][N:41](C(OC(C)(C)C)=O)[CH2:40][CH2:39]3)[CH:35]=[CH:36][CH:37]=2)O1>>[NH2:16][C:4]1[S:3][C:2]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N:38]3[CH2:39][CH2:40][NH:41][CH2:42][CH2:43]3)[CH:33]=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
Reactant 2
Product 1
Procedure
Following Example 278, Suzuki coupling of tert-butyl 2-bromo-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate and tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate gave 274 as a pale brown solid (18 mg, 19% over two steps). 1H NMR (400 MHz, d6-DMSO) δ 9.82 (s, 1H), 7.99 (s, 1H), 7.65 (s, 1H), 7.45 (s, 3H), 7.28 (dd, J=8, 7.5 Hz, 1H), 7.19 (d, J=7.5 Hz, 1H), 6.96 (dd, J=8, 2.5 Hz, 1H), 3.82 (s, 3H), 3.14 (t, J=5 Hz, 4H), 2.86 (t, J=5 Hz, 4H). Alkyl NH not seen. LCMS (ES+) m/z 384 (M+1)
Sources & evidence
- ORD record
- ord-a637326ca56e4e39affb9e6737e8ce77
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669361B2
Reaction notes
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