Hydrogen Peroxide → HCID 67451802, compound

HRID 869162Notes

Reaction equation

HRID 869162 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][C:13]([NH:17][CH2:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)([CH3:21])[CH3:20])=[CH:14][C:15]=2[CH3:16])=[CH:6][C:3]=1[C:4]#[N:5].OO.C([O-])([O-])=[O:32].[K+].[K+]>CS(C)=O.CCOC(C)=O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]([CH3:20])([CH3:21])[CH2:18][NH:17][C:13]2[N:12]=[N:11][C:10]([C:7]3[CH:6]=[C:3]([CH:2]=[CH:9][CH:8]=3)[C:4]([NH2:5])=[O:32])=[C:15]([CH3:16])[CH:14]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67452240HCID 67452240, compound

Product 1

HCID 67451802HCID 67451802, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of 2-fluoro-5-(6-(2-(4-fluorophenyl)-2-methylpropylamino)-4-methylpyridazin-3-yl)benzonitrile (0.80 g, 2.2 mmol, 1.0 equiv), 30% hydrogen peroxide (0.45 mL, 4.4 mmol, 2.0 equiv), and K2CO3 (600 mg, 4.4 mmol, 2.0 equiv) in DMSO (9.0 mL) was stirred for 1 hour. The mixture was diluted with EtOAc, washed with saturated NaCl, water and saturated NaCl again, and then dried over Na2SO4. Purification by reverse phase HPLC using a gradient of 20-70% CH3CN/water gave the desired product (420 mg, 51%) as a yellow solid. m/z=379.1 [M+H]+.

Workup

  1. washwashed with saturated NaCl, water and saturated NaCl again
  2. dry with materialdried over Na2SO4
  3. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-b572e9ccbc464bbe8ee95a35c23e89cf
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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