HCID 90067537, compound → HCID 90067631, compound
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:32])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=2)[CH:8]=[C:7]([NH:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[N:6]=1>CO.[Pd]>[OH:1][CH2:2][CH2:3][N:4]([CH3:32])[C:5]1[CH:10]=[C:9]([CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:15][CH2:16]2)[CH:8]=[C:7]([NH:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[N:6]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
tert-butyl 4-(2-((2-hydroxyethyl)(methyl)amino)-6-(4-methylpyridin-2-ylamino)pyridin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (130 mg, 0.29 mmol) was dissolved in MeOH (50 mL). The resulting solution was hydrogenated in H-Cube hydrogenation reactor, with 10% Pd/C cartridge under 40 bar, eluded 1 mL/min at 30° C. for two times. The resulting mixture was again hydrogenated under 50 bar, 1 mL/min at 30° C. for three times. The solution was concentrated in vacuo to give 100 mg (76%) of the title compound as a clear yellow gum. It was carried on as is. 1H NMR (400 MHz, CDCl3) δ 8.09 (d, J=5.2 Hz, 1H), 7.35 (s, 1H), 6.96 (s, 1H), 6.65 (d, J=5.2 Hz, 1H), 6.61 (s, 1H), 5.92 (s, 1H), 4.30 (d, J=53.7 Hz, 2H), 3.87 (t, J=5.0 Hz, 2H), 3.75 (t, J=5.0 Hz, 2H), 3.07 (s, 3H), 2.78 (t, J=12.6 Hz, 2H), 2.59-2.51 (m, 1H), 2.31 (s, 3H), 1.82 (d, J=12.7 Hz, 2H), 1.70-1.56 (m, 2H), 1.49 (s, 9H). LC-MS: m/z=442 (M+H+).
Workup
- customat 30° C.
- customwas again hydrogenated under 50 bar, 1 mL/min at 30° C. for three times
- concentrationThe solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-4619973722274acf9fa5f41e6600b402
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09399636B2
Reaction notes
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