HCID 59841042, compound → HCID 59841053, compound

HRID 221331Notes

Reaction equation

HRID 221331 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[O:11][C:12](=[N:21][C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=2)[C:13]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:9])(C)(C)C>N1CCCCC1.Cl.O1CCOCC1>[NH2:7][CH:8]([C:10]1[N:21]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=2)[C:12](=[O:11])[C:13]2[C:14](=[CH:16][CH:17]=[CH:18][C:19]=2[Cl:20])[N:15]=1)[CH3:9]

Participants

5

Reactant 1

HCID 59841042HCID 59841042, compound

Product 1

HCID 59841053HCID 59841053, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8082PiperidineSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of compound 169 (1.68 mmol) in piperidine (2 mL) was stirred for 3 h at ambient temperature. Evaporation of the reaction mixture to dryness under high vacuum gave a yellow foam. This foam was dissolved in a 4M solution of hydrogen chloride in 1,4-dioxane (4 mL) and stirred for 17 h at ambient temperature. The reaction mixture was then concentrated to dryness, basified with 10% aqueous potassium carbonate (40 mL) and extracted with MTBE (3×20 mL). Combining the organic extracts, drying over sodium sulfate and concentrating to dryness afforded a solid residue. This residue was dissolved in d-chloroform (5 mL), and warmed for 15 h at 50° C. After cooling to ambient temperature, the reaction mixture was washed with water (3×10 mL), dried over sodium sulfate and evaporated to dryness, affording a 98% yield of compound 170 as a white solid. m.p. 200-202° C.; 1H NMR (CDCl3) δ (ppm) 7.65 (m, 2H), 7.49 (m, 1H), 7.01 (t, 1H, J=6.6 Hz), 6.89 (m, 2H), 3.68 (m, 1H), 1.33 (d, 3H, J=6.6 Hz), 1.25 (s, 2H); m/z=336 (M+H). The reaction described above and compound 170 are shown below.

Workup

  1. customEvaporation of the reaction mixture to dryness under high vacuum
  2. customgave a yellow foam
  3. concentrationThe reaction mixture was then concentrated to dryness
  4. extractionextracted with MTBE (3×20 mL)
  5. dry with materialdrying over sodium sulfate
  6. concentrationconcentrating to dryness
  7. customafforded a solid residue
  8. temperaturewarmed for 15 h at 50° C
  9. temperatureAfter cooling to ambient temperature
  10. washthe reaction mixture was washed with water (3×10 mL)
  11. dry with materialdried over sodium sulfate
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-a5675eb72589471f85a6241df6be2022
Source dataset
uspto-grants-2012_06
Patent number
US08207153B2

Reaction notes

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