Hydrogen Peroxide → 5-{[(2S)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt
Reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[NH2:8][C@@H:9]([CH3:29])[CH2:10][NH:11][C:12]1[CH:13]=[C:14]([NH:20][C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[N:22]=2)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1.OO.[OH-:32].[Na+]>CS(C)=O>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[NH2:8][C@@H:9]([CH3:29])[CH2:10][NH:11][C:12]1[CH:13]=[C:14]([NH:20][C:21]2[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[N:22]=2)[C:15]([C:18]([NH2:19])=[O:32])=[N:16][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-{[(2S)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile TFA salt (166 mg, 0.404 mmol) in DMSO (3 ml) were added hydrogen peroxide (35% aqueous solution, 0.053 ml, 0.61 mmol) and sodium hydroxide (4.0 M aqueous solution, 0.32 mL, 1.3 mmol) at 20° C. After 16 hour, the reaction mixture was purified directly by reverse phase HPLC (acetonitrile/water with 0.1% TFA) to give 5-{[(2S)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt. MS ESI calc'd. for C16H23N6O [M+H]+ 315. found 315. 1H NMR (500 MHz, CD3OD) δ 7.81 (s, 1H), 7.59 (s, 1H), 7.10 (s, 1H), 6.90 (s, 1H), 3.72-3.49 (m, 1H), 3.52-3.33 (m, 2H), 2.53 (s, 3H), 2.40 (s, 3H), 1.39 (d, J=6.6 Hz, 3H).
Workup
- customthe reaction mixture was purified directly by reverse phase HPLC (acetonitrile/water with 0.1% TFA)
Sources & evidence
- ORD record
- ord-20b46d6baa5247218ab5553aa2648c65
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216173B2
Reaction notes
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