Hydrogen Peroxide → HCID 71544548, compound

HRID 878414Notes

Reaction equation

HRID 878414 reaction equation
[NH2:1][CH:2]([CH2:21][CH3:22])[CH2:3][NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)[CH:6]=1.[OH:23]O.[OH-].[K+]>CS(C)=O>[NH2:1][CH:2]([CH2:21][CH3:22])[CH2:3][NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]([NH2:12])=[O:23])=[C:7]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 89486743HCID 89486743, compound

Product 1

HCID 71544548HCID 71544548, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-[(2-aminobutyl)amino]-4-[(6-methylpyridin-2-yl)amino]pyridine-3-carbonitrile (24 mg, 0.081 mmol) in DMSO (1 mL) was added hydrogen peroxide (35% aqueous solution, 0.071 mL, 0.81 mmol) and potassium hydroxide (45 mg, 0.81 mmol). The reaction mixture was stirred for 16 hours, and then was filtered and purified directly via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to afford 6-[(2-aminobutyl)amino]-4-[(6-methylpyridin-2-yl)amino]pyridine-3-carboxamide. MS ESI calc'd. for C16H23N6O [M+H]+ 315. found 315. 1H NMR (500 MHz, CD3OD) δ 8.34 (s, 1H), 7.79 (s, 1H), 7.55 (t, J=8.0 Hz, 1H), 6.80 (d, J=7.5 Hz, 1H), 6.73 (d, J=8.0 Hz, 1H), 3.39 (dd, J=14 Hz, J=4.5 Hz, 1H), 3.18 (dd, J=13.5 Hz, J=8.0 Hz, 1H), 2.96-2.90 (m, 1H), 2.49 (s, 3H), 1.66-1.56 (m, 1H), 1.46-1.38 (m, 1H), 1.01 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationwas filtered
  2. custompurified directly via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

Sources & evidence

ORD record
ord-9b9e7a12c17b40518166a1853945fa9a
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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