1-Methylpiperazine → HCID 67457051, compound

HRID 1852947Notes

Reaction equation

HRID 1852947 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([B:13]2[O:17]C(C)(C)C(C)(C)[O:14]2)[CH:10]=[N:9]1)(=O)=O.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C)C=O.ClCCl>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([B:13]([OH:14])[OH:17])[CH:10]=[N:9]2)[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 86685293HCID 86685293, compound

Product 1

HCID 67457051HCID 67457051, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl methanesulfonate (0.080 g, 0.253 mmol) in 0.5 mL N,N-dimethylformamide was added 1-methylpiperazine (0.281 mL, 2.53 mmol) and the reaction was sealed under nitrogen and heated to 50° C. for 2.5 hours. The reaction mixture was diluted with dichloromethane (3 mL) and then loaded directly onto a silica gel column pre-wetted and eluted with 15% methanol in dichloromethane containing 1% ammonium hydroxide to afford 1-(2-(4-methylpiperazin-1-yl)ethyl)-1H-pyrazol-4-ylboronic acid (0.038 g, 0.160 mmol, 63% yield) as a result of hydrolysis on silica in the presence of methanol and ammonium hydroxide. MS (apci) m/z=239.1 (M+H).

Workup

  1. customthe reaction was sealed under nitrogen
  2. washeluted with 15% methanol in dichloromethane containing 1% ammonium hydroxide

Sources & evidence

ORD record
ord-5cf00ddb536e42808a82bff6130fbc1c
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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