Piperazine → HCID 59485123, compound

HRID 1850506Notes

Reaction equation

HRID 1850506 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[C:7]([CH3:19])=[C:8]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.Cl[C:22]1[N:27]2[N:28]=[CH:29][CH:30]=[C:26]2[N:25]=[C:24]([CH3:31])[CH:23]=1.C(N(C(C)C)CC)(C)C.N1CCNCC1>C(OCC)(=O)C.C1COCC1>[CH3:31][C:24]1[CH:23]=[C:22]([N:16]2[CH2:15][CH2:14][N:13]([C:8]3[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]4[O:3][C:2]([CH3:20])([CH3:1])[CH2:6][C:5]=4[C:7]=3[CH3:19])[CH2:18][CH2:17]2)[N:27]2[N:28]=[CH:29][CH:30]=[C:26]2[N:25]=1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 104872877-Chloro-5-methylpyrazolo[1,5-a]pyrimidineHCID 667597311-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine

Product 1

HCID 59485123HCID 59485123, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of THF (2 mL) containing 1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (274 mg, 1.0 mmol) synthesized in Reference Example 61, 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine (200 mg, 1.2 mmol) and diisopropylethylamine (0.42 mL) were added, and the mixture was heated to reflux for 2 hours. After addition of piperazine (42 mg, 0.50 mmol) thereto, the mixture was further heated to reflux for 1 hour. The reaction solution was diluted with ethyl acetate, and washed with water and saturated saline. The organic layer was dried using magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 7:3). The obtained solid was recrystallized from ethanol-water to obtain 140 mg of the title compound (yield 35%). Melting point was 180 to 182° C. (ethanol-water).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 hours
  4. temperaturethe mixture was further heated
  5. temperatureto reflux for 1 hour
  6. washwashed with water and saturated saline
  7. customThe organic layer was dried
  8. customThe solvent was removed under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 7:3)
  10. customThe obtained solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-248cfaff780a4320b0970c1e229f1f2a
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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