[4-(Piperazin-1-yl)phenyl]boronic acid → N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(1-piperazinyl)phenyl]-1H-indazole-4-carboxamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:28])[NH:20][C:21]([CH3:27])=[CH:22][C:23]=2[CH2:24]CC)=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[N:29]1([C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:27])[NH:20][C:19](=[O:28])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=[C:2]([C:38]2[CH:37]=[CH:36][C:35]([N:29]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]3)=[CH:40][CH:39]=2)[CH:3]=1)=[O:15]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a similar manner as described for example 8 from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (80 mg, 0.192 mmol) and [4-(1-piperazinyl)phenyl]boronic acid (59 mg, 0.288 mmol). The product was collected as a white solid (34 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (br. s., 1H) 8.66 (br. s., 1H) 8.33 (s, 1H) 8.00 (s, 1H) 7.82 (s, 1H) 7.73-7.76 (m, 1H) 7.72 (s, 1H) 7.01-7.09 (m, 2H) 5.89 (s, 1H) 5.14 (dt, J=13.33, 6.60 Hz, 1H) 4.39 (br. s., 1H) 4.38 (br. s., 1H) 3.38-3.52 (m, 4H) 3.09-3.14 (m, 1H) 3.00-3.09 (m, 3H) 2.81-2.90 (m, 1H) 2.21 (s, 3H) 2.13 (s, 3H) 1.50 (s, 3H) 1.48 (s, 3H). LC-MS (ES) m/z=499.4 [M+H]+
Workup
- customThe product was collected as a white solid (34 mg, 35%)
Sources & evidence
- ORD record
- ord-79a4edc0b8f6465a96284e9e949e0a70
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846935B2
Reaction notes
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