5-Chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methylbenzoic acid → 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-N-((4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methylbenzamide formate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]([CH2:18][CH3:19])[CH:13]2[CH2:16][N:15]([CH3:17])[CH2:14]2)[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.[NH2:21][CH2:22][C:23]1[C:24](=[O:33])[NH:25][C:26]([CH3:32])=[CH:27][C:28]=1[CH:29]([CH3:31])[CH3:30]>>[CH:7]([OH:9])=[O:8].[Cl:1][C:2]1[CH:3]=[C:4]([N:12]([CH2:18][CH3:19])[CH:13]2[CH2:16][N:15]([CH3:17])[CH2:14]2)[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([NH:21][CH2:22][C:23]1[C:24](=[O:33])[NH:25][C:26]([CH3:32])=[CH:27][C:28]=1[CH:29]([CH3:30])[CH3:31])=[O:9]Participants
Reactant 2
Product 1
Procedure
The same way for the previous compound 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)benzamide formate prepared, the titled compound prepared using 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methylbenzoic acid and 3-(Aminomethyl)-6-methyl-4-(propan-2-yl)-1,2-dihydropyridin-2-one HCl salt. After purification by reverse phase HPLC/MS (CAN-H2O containing 0.1% formic acid), the titled compound was obtained. 1H-NMR (500 MHz, CD3OD) δ ppm 8.43-8.25 (br, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.08 (d, J=2.0 Hz, 1H), 6.25 (s, 1H), 4.52 (s, 2H), 4.40-4.34 (m, 1H), 4.29-4.21 (br, 2H), 3.90-3.79 (br, 2H), 3.48-3.40 (m, 1H), 3.00 (q, J=7.0 Hz, 2H), 2.92 (s, 3H), 2.34 (s, 3H), 2.28 (s, 3H), 1.24 (d, J=7.0 Hz, 6H), 0.90 (t, J=7.0 Hz, 3H). MS (ES) (M+H) 445.47.
Workup
- customAfter purification by reverse phase HPLC/MS (CAN-H2O containing 0.1% formic acid)
Sources & evidence
- ORD record
- ord-845818eb86484a64b932b759be8cd0ee
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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