Hydrogen Peroxide → HCID 71522868, compound

HRID 1470332Notes

Reaction equation

HRID 1470332 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[N:19]=2)[CH:10]=1.[OH-:26].[Na+].OO>CS(C)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]([NH2:14])=[O:26])=[C:11]([NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[N:19]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 90355855HCID 90355855, compound

Product 1

HCID 71522868HCID 71522868, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
35 °C

Procedure

To a mixture of rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(4,6-dimethylpyridin-2-yl)amino]benzonitrile (70 mg, 0.21 mmol) and sodium hydroxide (4.0 M in water, 0.25 mL, 1.0 mmol) in DMSO (2.5 mL) was added hydrogen peroxide (30% aqueous solution, 0.10 mL, 0.98 mmol). The reaction mixture was heated to 35° C. After 40 minutes, the reaction mixture was filtered and purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to give rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(4,6-dimethylpyridin-2-yl)amino]benzamide. MS ESI calc'd. for C20H28N5O [M+H]+ 354. Found 354. 1H NMR (300 MHz, CD3OD) δ 7.67 (s, 1H), 7.47 (d, J=8.7 Hz, 1H), 6.55 (m, 2H), 6.21-6.25 (m, 1H), 3.55-3.52 (m, 1H), 3.17 (br s, 1H), 2.37 (s, 3H), 2.22 (s, 3H), 1.77-1.42 (m, 8H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. custompurified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

Sources & evidence

ORD record
ord-abd5cd9ed76542a98f0aabdfc15f4121
Source dataset
uspto-grants-2015_04
Patent number
US09006444B2

Reaction notes

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