Sodium Hydroxide → HCID 57418389, compound

HRID 1868134Notes

Reaction equation

HRID 1868134 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[C:26]([F:29])([F:28])[F:27])[CH2:15][C@H:14]2[CH3:30])(=[O:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C(O)(C(F)(F)F)=[O:32].OS(O)(=O)=O.[OH-].[Na+]>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[C:26]([F:27])([F:29])[F:28])[CH2:15][C@H:14]2[CH3:30])(=[O:12])=[O:11])=[CH:6][C:3]=1[C:4]([NH2:5])=[O:32]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 68547960HCID 68547960, compoundHCID 86586073TFA sulfuric acid

Product 1

HCID 57418389HCID 57418389, compoundYield 58.4%

Procedure

To a flask containing 2-fluoro-5-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)benzonitrile (399 mg, 0.90 mmol) was added a mixture of TFA/H2SO4 (4 mL, 2/2 v/v). The reaction mixture was stirred at room temperature for 5 days. Reaction was complete as determined by TLC. Slowly poured the reaction mixture to the ice, then neutralized the reaction mixture with 3N NaOH until pH=7-8, extracted with EtOAc (2×150 mL). The combined organic layer washed with sat. brine and dried over Na2SO4, and concentrated under reduced pressure. Purification by prep HPLC under neutral condition to yield 2-fluoro-5-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)benzamide as a white solid (243.7 mg, 58.4%). HRMS: calcd for C19H18F5N3O3S+H+, 464.10618. found (ESI-FTMS, [M+H]1+), 464.10639.

Workup

  1. additionwas added
  2. customReaction
  3. extractionextracted with EtOAc (2×150 mL)
  4. washThe combined organic layer washed with sat. brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by prep HPLC under neutral condition

Sources & evidence

ORD record
ord-bdcb28b05c4e44ab9b13b7767cc9adc6
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…