Acetic Acid → HCID 67545688, compound

HRID 2176132Notes

Reaction equation

HRID 2176132 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.Cl.[CH:16]12[NH:24][CH:20]([CH2:21][CH2:22][CH2:23]1)[CH2:19][C:18](=O)[CH2:17]2.Cl.C(O)(=O)C>>[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[NH:11][C:18]1[CH2:17][CH:16]3[NH:24][CH:20]([C:19]2=1)[CH2:21][CH2:22][CH2:23]3

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochlorideHCID 197915239-Azabicyclo[3.3.1]nonan-3-one--hydrogen chloride (1/1)

Product 1

HCID 67545688HCID 67545688, compound

Procedure

In a 30 mL microwave reaction tube were combined 4-(trifluoromethoxy)phenyl-hydrazine hydrochloride (1062 mg, 5.0 mmol; Maybridge), 9-azabicyclo[3.3.1]nonan-3-one hydrochloride (878 mg, 5.0 mmol; Accela ChemBio), and 1 N HCl in acetic acid (15 mL, 15 mmol; Aldrich). The reaction mixture was microwaved at 150° C. (Biotage Personal Chemistry, maximum 300 W) for 15 minutes, then cooled to room temperature. The solvent was removed, and the residue was dissolved in water (20 mL) and basified with solid potassium carbonate to ˜pH 12. This solution was extracted with dichloromethane (3×50 mL), and the combined organic phases were dried over magnesium sulfate. After removing the solvent under vacuum, the residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 3:1) to afford the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.33-1.52 (m, 2H), 1.64-1.78 (m, 2H), 1.89-2.06 (m, 2H), 2.68 (d, J=17 Hz, 1H), 3.25-3.34 (m, 1H), 3.62 (t, J=5 Hz, 1H), 4.43 (t, J=3 Hz, 1H), 6.93 (ddd, J=9, 2, 1 Hz, 1H), 7.22 (d, J=1 Hz, 1H), 7.31 (d, J=9 Hz, 1H); MS (DCI/NH3) m/z 297 (M+H)+.

Workup

  1. customIn a 30 mL microwave reaction tube were combined
  2. customThe reaction mixture was microwaved at 150° C. (Biotage Personal Chemistry, maximum 300 W) for 15 minutes
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in water (20 mL)
  5. extractionThis solution was extracted with dichloromethane (3×50 mL)
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. customAfter removing the solvent under vacuum
  8. customthe residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 3:1)

Sources & evidence

ORD record
ord-82aa5ff0bb4d4c99b5b05e18567a7278
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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