6-(Morpholino)pyridine-3-boronic Acid (contains varying amounts of Anhydride) → 1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-morpholinyl)-3-pyridinyl]-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][CH2:25][CH3:26])=[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[N:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[CH3:12][CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([C:38]3[CH:39]=[N:40][C:35]([N:29]4[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)=[CH:36][CH:37]=3)[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]3[C:19](=[O:28])[NH:20][C:21]([CH3:27])=[CH:22][C:23]=3[CH2:24][CH2:25][CH3:26])=[O:15])[C:5]=2[CH:6]=[N:7]1)[CH3:13]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 (100 mg, 0.225 mmol) and [6-(4-morpholinyl)-3-pyridinyl]boronic acid (70 mg, 0.337 mmol). The final product was collected as a white solid (98 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.46 (br. s., 1H) 8.68 (d, J=2.53 Hz, 2H) 8.37 (s, 1H) 8.07-8.12 (m, 2H) 7.84 (d, J=1.01 Hz, 1H) 6.98 (d, J=8.84 Hz, 1H) 5.91 (s, 1H) 5.14 (quin, J=6.57 Hz, 1H) 4.42 (d, J=4.80 Hz, 2H) 3.71-3.76 (m, 4H) 3.50-3.56 (m, 4H) 2.52-2.56 (m, 2H) 2.13 (s, 3H) 1.51-1.58 (m, 2H) 1.51 (s, 3H) 1.49 (s, 3H) 0.88 (t, J=7.33 Hz, 3H). LC-MS (ES) m/z=529.0 [M+H]+
Workup
- customThe final product was collected as a white solid (98 mg, 81%)
Sources & evidence
- ORD record
- ord-01aad9561ecd48a5ac81344e0ff7c081
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846935B2
Reaction notes
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