Hydrogen Peroxide → HCID 70159227, compound

HRID 1278580Notes

Reaction equation

HRID 1278580 reaction equation
[CH2:1]([N:3](CC)[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=3)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=O)[CH3:2].[C:34](=[O:37])([O-])[O-:35].[Na+].[Na+].OO.[OH2:42]>C(O)C>[CH2:1]([NH:3][CH2:4][CH3:6])[CH3:2].[C:30]([C:26]1[CH:25]=[C:24]([C:12]2([C:9]3[N:8]=[CH:7][C:6]([C:34]([OH:35])=[O:37])=[CH:11][N:10]=3)[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:16][CH2:17]2)[CH:29]=[CH:28][CH:27]=1)(=[O:42])[NH2:31]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 10340Sodium CarbonateHCID 70157614HCID 70157614, compound

Product 1

HCID 70159227HCID 70159227, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 2-[4-(3-cyano-phenyl)-1-(2-methyl-pentyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid diethylamide (90 mg, 0.20 mmol) in 1.5 mL ethanol (EtOH) at room temperature was added a 3 N solution of sodium carbonate (Na2CO3) (0.5 mL) and a 30% solution of hydrogen peroxide (H2O2) (0.14 mL). The reaction mixture was stirred for 24 hours, diluted with 10 mL water and extracted with EtOAc (3×15 mL). The combined organic layers were dried and concentrated. The crude material was purified by flash chromatography to afford 30 mg (35%) of the desired amide. 1HNMR (400 MHz, CDCl3) δ 8.71 (s, 2H), 7.89 (s, 1H), 7.58-7.51 (comp, 2H), 7.31 (t, 1H), 6.26 (br s, 1H), 5.88 (br s, 1H), 3.53-3.51 (comp, 2H), 3.26-3.25 (comp, 2H), 3.03-3.00 (comp, 2H), 2.75 (br s, 2H), 2.44-2.42 (comp, 2H), 2.15-2.02 (comp, 4H), 1.63-1.61 (comp, 1H), 1.36-1.16 (comp, 9H), 1.07-0.97 (comp, 1H), 0.87-0.83 (comp, 6H); MS (M+1) 466.3.

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-5af9f11eec644371b739d6c826e96d14
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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