Piperazine → HCID 66758934, compound

HRID 1507818Notes

Reaction equation

HRID 1507818 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 50941489HCID 50941489, compound

Product 1

HCID 66758934HCID 66758934, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-amino-7-chloro-2-(4-fluorophenyl)-oxazolo[5,4-d]pyrimidine X (50 mg, 0.19 mmol) in dioxane (5 ml) was added diisopropylethylamine (0.28 mmol, 47 μL) and a piperazine derivative (0.28 mmol). The reaction was stirred at 70° C. for 6 hours after which the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 2% CH3OH in CH2Cl2), yielding the pure title compounds which were characterized by their mass spectra as indicated below:

Workup

  1. customwas removed in vacuo
  2. customThe resulting residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-bcc079e6c5484ec8ad4f82e257183546
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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