Hydrochloric Acid → HCID 22179341, compound

HRID 1795815Notes

Reaction equation

HRID 1795815 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[C:16](Cl)[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:9]=2[C:8]1=[O:27].C([O:41][C:42]([NH:44][CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)=O)(C)(C)C.O1CCOC[CH2:52]1.Cl>C(OCC)(=O)C>[C:42]([NH:44][CH:45]1[CH2:50][CH2:49][N:48]([C:16]2[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:9]3[C:8](=[O:27])[N:7]([CH2:6][C:5]4[CH:4]=[C:3]([C:2]([F:36])([F:35])[F:1])[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=4)[CH2:14][CH2:13][CH2:12][O:11][C:10]=3[N:15]=2)[CH2:47][CH2:46]1)(=[O:41])[CH3:52]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 7238334-(N-Boc-amino)piperidineHCID 22179334HCID 22179334, compound

Product 1

HCID 22179341HCID 22179341, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-7-(2-methylphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (47.6 mg), 4-(t-butoxycarbonylamino)piperidine (45.1 mg), and 1,4-dioxane (1 mL) was stirred at 150° C. for 3 hours. The solvent was then removed to obtain a residue. To this residue, a 3 mol/L ethyl acetate solution of hydrogen chloride (1 mL) was added and the mixture was stirred at room temperature for 1 hour. The solvent was removed and the resulting residue was dissolved in tetrahydrofuran (1 ml). While the solution was chilled on an ice bath, triethylamine (60 μl) and acetylchloride (30 μl) were added, and the mixture was stirred at room temperature for 30 min. This was followed by the addition of ethyl acetate, and the mixture was washed with water and was then dried on anhydrous sodium sulfate. Subsequently, the solvent was removed and the resulting residue was purified on a silica gel column chromatography (ethyl acetate) to obtain 9-[4-(acetylamino)piperidine-1-yl]-5-[3,5-bis(trifluoromethyl)benzyl]-7-(2-methylphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (19.2 mg, 34%).

Workup

  1. customThe solvent was then removed
  2. customto obtain a residue
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. customThe solvent was removed
  5. dissolutionthe resulting residue was dissolved in tetrahydrofuran (1 ml)
  6. temperatureWhile the solution was chilled on an ice bath
  7. additiontriethylamine (60 μl) and acetylchloride (30 μl) were added
  8. stirringthe mixture was stirred at room temperature for 30 min
  9. additionThis was followed by the addition of ethyl acetate
  10. washthe mixture was washed with water
  11. dry with materialwas then dried on anhydrous sodium sulfate
  12. customSubsequently, the solvent was removed
  13. customthe resulting residue was purified on a silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-259c5d1083ae4e5db56e55d37af459de
Source dataset
uspto-grants-2006_04
Patent number
US07030107B2

Reaction notes

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