Hydrogen Peroxide → 5-{[(2-Aminoethyl)sulfonyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

HRID 1504894Notes

Reaction equation

HRID 1504894 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([NH:7][C:8]1[CH:9]=[N:10][C:11]([C:23]#[N:24])=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[N:16]=2)[CH:13]=1)(=[O:6])=[O:5].[OH-:25].[K+].OO>CS(C)=O>[NH2:1][CH2:2][CH2:3][S:4]([NH:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[N:16]=2)[C:11]([C:23]([NH2:24])=[O:25])=[N:10][CH:9]=1)(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 867317672-amino-N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)-amino]pyridin-3-yl}ethanesulfonamide

Product 1

HCID 867317665-{[(2-Aminoethyl)sulfonyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-amino-N-{6-cyano-5-[(4,6-dimethylpyridin-2-yl)-amino]pyridin-3-yl}ethanesulfonamide (78 mg, 0.23 mmol) in DMSO (1.8 mL) was added potassium hydroxide (63 mg, 1.1 mmol) and hydrogen peroxide (35% w/w in water, 0.20 mL, 2.3 mmol). The reaction mixture was stirred for 1 hour. The reaction mixture was filtered and the filtrate directly purified by reverse phase HPLC to afford 5-{[(2-aminoethyl)sulfonyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C15H21N6O3S [M+H]+ 365. found 365. 1H NMR (500 MHz, DMSO-d6) δ 11.33 (s, 1H), 8.45 (d, J=2.3 Hz, 1H), 7.80 (s, 1H), 7.46 (d, J=2.3 Hz, 1H), 7.12 (s, 1H), 6.51 (s, 1H), 6.47 (s, 1H), 2.92 (t, J=6.1 Hz, 2H), 2.89-2.81 (m, 2H), 2.32 (s, 3H), 2.18 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-7efc4a52bf404d61b85b06d918534e11
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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