6-(Boc-methylamino)pyridine-3-boronic acid pinacol ester → 1-(1-Isopropyl-3-methyl-1h-pyrazol-4-yl)-3-methyl-8-(6-methylamino-pyridin-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:25])[C:13](=[O:24])[N:14]([C:15]4[C:16]([CH3:23])=[N:17][N:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:26]([N:33](C)[C:34]1[N:39]=[CH:38][C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][CH:35]=1)(OC(C)(C)C)=O>>[CH:20]([N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:37]5[CH:38]=[N:39][C:34]([NH:33][CH3:26])=[CH:35][CH:36]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:25])[C:13]2=[O:24])[C:16]([CH3:23])=[N:17]1)([CH3:21])[CH3:22]Participants
Reactant 2
Product 1
Procedure
The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1-isopropyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate G, 58.8 mg, 0.147 mmol) and 6-(N-boc-methylamino)pyridine-3-boronic acid pinacol ester (Alfa Aesar, Heysham, UK, 58.8 mg, 0.176 mmol) to give crude boc-protected title compound that is treated for 25 min at rt with trifluoroacetic acid (1.5 ml) and then purified by prep. HPLC to give the title compound as a light yellow solid. (HPLC: tR 2.21 min (Method A); M+H=428 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.90 (s, 1H), 8.23-8.14 (m, 2H), 8.05-7.98 (m, 1H), 7.87-7.79 (m, 1H), 7.48-7.37 (m, 2H), 6.78-6.70 (m, 1H), 6.49-6.42 (m, 1H), 4.61-4.50 (m, 1H), 3.56 (s, 3H), 2.77 (d, 3H), 1.95 (d, 3H), 1.51-1.45 (m, 6H))
Workup
- customThe title compound was synthesized in a similar manner
Sources & evidence
- ORD record
- ord-ded938c3e6fb4a1bb91d68a59a9c95f4
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476294B2
Reaction notes
Loading…