1-Methylpiperazine → HCID 66648568, compound

HRID 417938Notes

Reaction equation

HRID 417938 reaction equation
[CH3:1][C:2]1([CH3:24])CN[C:6](=[O:9])[C:5]2[S:10][C:11]([N:13]3[C:18]4[CH:19]=[C:20](O)[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14]3)=[N:12][C:4]=2[CH2:3]1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[CH3:32]C(C)([O-])C.[Na+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1([CH3:32])[CH2:3][C:4]2[N:12]=[C:11]([N:13]3[C:18]4[CH:19]=[C:20]([N:29]5[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]5)[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14]3)[S:10][C:5]=2[C:6](=[O:9])[CH2:24]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 23676156Sodium t-butoxideHCID 24956160HCID 24956160, compound

Product 1

HCID 66648568HCID 66648568, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

Using Example 7 (50 mg, 0.14 mmol), 1-methylpiperazine (0.12 mL, 1.15 mmol), sodium tert-butoxide (41 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.007 mmol) and (But)3PBF4 (4 mg, 0.014 mmol) in THF (3 mL) heated to 140° C. under microwave irradiation for 20 min. The crude material was purified by prep HPLC to give the title compound as an off-white solid (6 mg, 8%). δH (CDCl3) 1.15 (6H, s), 2.37 (3H, s), 2.42 (2H, s), 2.56-2.65 (4H, m), 2.75 (2H, s), 3.09-3.18 (4H, m), 4.25-4.31 (2H, m), 4.18-4.25 (2H, m), 6.72 (1H, dd, J 8.9, 2.6 Hz), 6.87 (1H, d, J 8.9 Hz), 7.41 (1H, d, J 2.8 Hz). LCMS (ES+) 413 (M+H)+.

Workup

  1. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-a8a38628212841f1b9639e4bc77a6c02
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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