Triethylamine → HCID 86691868, compound

HRID 517702Notes

Reaction equation

HRID 517702 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1.C(N(CC)CC)C.[CH3:25][C@@H:26]1[NH:31][CH2:30][CH2:29][NH:28][C:27]1=[O:32]>C(#N)C>[CH3:25][C@@H:26]1[N:31]([CH2:2][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[N:6]=[N:5][N:4]=2)[CH2:30][CH2:29][NH:28][C:27]1=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13190462(3S)-3-Methylpiperazin-2-oneHCID 43134746HCID 43134746, compound

Product 1

HCID 86691868HCID 86691868, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-(chloromethyl)-1-[4-(trifluoromethyl)phenyl]-1H-tetrazole (500 mg, 1.90 mmol, commercially available from UkrOrgSynthesis, Kiev, Ukraine) in acetonitrile (8 mL) was added triethylamine (0.796 mL, 5.71 mmol) and (3S)-3-methyl-2-piperazinone (239 mg, 2.09 mmol, commercially available, for example from Sigma Aldrich, St Louis, USA). The reaction mixture was heated to 120° C. for 20 min. The reaction mixture was concentrated in vacuo and the crude product purified by reverse phase chromatography (Biotage SP4). The relevant fractions were combined, concentrated and dried in vacuo to yield the title compound as white crystals (349 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product purified by reverse phase chromatography (Biotage SP4)
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2646538a261b41bc817ac9178e3f1233
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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