Hydrogen Peroxide → HCID 68697894, compound

HRID 1990892Notes

Reaction equation

HRID 1990892 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S1C2C=CC=CC=2N=C1NC1CCN(CC2C3C(=CC=CC=3)C=CC=2[O:53]CC)CC1.C(=O)([O-])[O-].[K+].[K+].OO.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([C:24](=[O:53])[NH2:25])=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 66912254HCID 66912254, compoundHCID 86607625Benzothiazol-2-yl-[1-(2-ethoxy-naphthalen-1-ylmethyl)-piperidin-4-yl]-amine

Product 1

HCID 68697894HCID 68697894, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 4-(5-cyano-benzooxazol-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.03 g, 3.01 mmol, 1.0 equiv; intermediate T (2-(piperidin-4-ylamino)-benzooxazole-5-carbonitrile)/step 1) and 0.084 g (0.6 mmol) of potassium carbonate in DMSO (5 mL) was added a solution of 35% hydrogen peroxide in water (0.53 mL, 0.59 g, 6.02 mmol, 2.0 equiv) and the reaction mixture stirred at ambient temperature for 24 h. The solution was poured on crashed ice, the reaction mixture extracted with dichloromethane/2-propanol (4:1, 3×50 mL) and the combined organic phases dried over MgSO4. The organic solvent was evaporated under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with a gradient of dichloromethane/methanol (100:0→95:5) containing 33% of NH4OH to yield 1.05 g (97%) of the title compound. MS (ESI): 361.2 [M+H]+.

Workup

  1. additionThe solution was poured
  2. extractionthe reaction mixture extracted with dichloromethane/2-propanol (4:1, 3×50 mL)
  3. dry with materialthe combined organic phases dried over MgSO4
  4. customThe organic solvent was evaporated under reduced pressure
  5. customthe crude reaction product
  6. custompurified with column chromatography on silica eluting with a gradient of dichloromethane/methanol (100:0→95:5)
  7. additioncontaining 33% of NH4OH

Sources & evidence

ORD record
ord-fd1bbf8c43ab42ae803c01823de465c6
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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