Hydrochloric Acid → HCID 69277010, compound

HRID 915577Notes

Reaction equation

HRID 915577 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:9]=1)=O.C([O-])([O-])=O.[K+].[K+].[ClH:34]>CO.O>[ClH:34].[ClH:34].[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][NH2:5])=[CH:9][C:10]=1[S:16]([N:19]1[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]1)(=[O:17])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58958622HCID 58958622, compound

Product 1

HCID 69277010HCID 69277010, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,2,2-trifluoro-N-(2-{4-methoxy-3-[(4-methylpiperazin-1-yl)sulfonyl]-phenyl}ethyl) acetamide (from Step 2), (1.25 g, 3.05 mmol) in MeOH (30 mL) and H2O (8 mL) was added K2CO3 (2.11 g, 15.3 mmol), and the solution was stirred at 60° C. for 2 h. After cooling to rt, the MeOH was evaporated under reduced pressure. The remaining aqueous mixture was extracted with CH2Cl2 (6×50 mL), and the combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then dissolved in MeOH, and 4 equivalents of 1 N HCl in MeOH were added causing the formation of a white precipitate. The solvent was removed under reduced pressure, and the resulting solid was recrystallized from MeOH/Et2O to give the title compound [assumed to be the bis-HCl salt] as a white solid (457 mg, 48%). 1H NMR (400 MHz, CD3OD) δ 2.29 (s, 3H), 2.48 (broad t, 4H), 2.78 (dd, 2H), 2.87-2.92 (m, 2H), 3.23 (broad t, 4H), 3.91 (s, 3H) 7.16 (d, 1H), 7.47 (dd, 1H), 7.68 (d, 1H); ES-MS m/z (MH+) 314.2, HPLC RT (min) 0.70.

Workup

  1. temperatureAfter cooling to rt
  2. customthe MeOH was evaporated under reduced pressure
  3. extractionThe remaining aqueous mixture was extracted with CH2Cl2 (6×50 mL)
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was then dissolved in MeOH
  8. customThe solvent was removed under reduced pressure
  9. customthe resulting solid was recrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-3e685626902e4cc0b80cd896b016a20b
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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