3-(1-(2,4-bis(trifluoromethyl)phenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide → HCID 68452832, compound

HRID 2357669Notes

Reaction equation

HRID 2357669 reaction equation
F[C:2](F)(F)[C:3]1[CH:8]=[C:7](C(F)(F)F)[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]3[CH:24]=[C:25]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:26]([NH:28]C3CC3)=[O:27])=[CH:20][CH:21]=2)[CH:16]=[N:15][N:14]=1.O[O:39][S:40]([O-:42])=O.[K+].[CH3:44]O.O>>[CH3:35][C:34]1[CH:33]=[CH:32][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][C:23]=1[C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[C:13]([C:4]1[CH:5]=[CH:6][C:7]([S:40]([CH3:44])(=[O:42])=[O:39])=[CH:8][C:3]=1[CH3:2])=[N:14][N:15]=[CH:16]2

Participants

4

Reactant 3

HCID 118489893-(1-(2,4-bis(trifluoromethyl)phenyl)phthalazin-6-yl)-N-cyclopropyl-4-methylbenzamideHCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 68452832HCID 68452832, compound

Conditions

Temperature
0 °C

Procedure

A solution of 4-methyl-3-(1-(2-methyl-4-(methylthio)phenyl)phthalazin-6-yl)benzamide (170 mg, 0.43 mmol, Method D) in 2 mL of 10/1 methanol/H2O at 0° C. was treated with oxone (262 mg, 0.43 mmol). The mixture stirred at 0° C. for 1 h and then warmed up to RT for 1 h. The reaction was quenched with 20 mL sodium sulfite (sat.) and extracted with 10% MeOH in dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude material was purified by HPLC to give 4-methyl-3-(1-(2-methyl-4-(methylsulfonyl)phenyl)phthalazin-6-yl)benzamide as a white solid. Found MS (ES+)=432.1 (M+H+).

Workup

  1. temperaturewarmed up to RT for 1 h
  2. customThe reaction was quenched with 20 mL sodium sulfite (sat.)
  3. extractionextracted with 10% MeOH in dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-245186e08d0c4d5e9a7850c4c6c7bdd7
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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