1-Methylpiperazine → HCID 68528916, compound

HRID 1036370Notes

Reaction equation

HRID 1036370 reaction equation
CC1C=CC(S(O[C:12]2[C:13]3[CH2:23][CH2:22][CH2:21][C:20]4[N:24]([CH3:27])[N:25]=[CH:26][C:19]=4[C:14]=3[N:15]=[C:16]([NH2:18])[N:17]=2)(=O)=O)=CC=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(#N)C>[CH3:27][N:24]1[C:20]2[CH2:21][CH2:22][CH2:23][C:13]3[C:12]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)=[N:17][C:16]([NH2:18])=[N:15][C:14]=3[C:19]=2[CH:26]=[N:25]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86637696HCID 86637696, compound

Product 1

HCID 68528916HCID 68528916, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the product from Example 8C (0.048 g, 0.12 mmol) and N-methylpiperazine (0.25 g, 0.25 mmol) in acetonitrile (1 mL) was heated in a microwave at 160° C. for 1 hour. The reaction mixture was partitioned in dichloromethane/water, the organic layer was separated, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel, eluting with 5% methanol/dichloromethane/1% ammonium hydroxide to yield the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.84 (m, 1 H), 5.96 (m, 2 H), 3.76 (s, 3 H), 3.07 (m, 4 H), 2.93 (t, J=6.27 Hz, 2 H), 2.59 (m, 2 H), 2.43 (m, 4 H), 2.22 (s, 3 H), 1.90 (m, 2 H); MS (ESI+) m/z 314 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned in dichloromethane/water
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 5% methanol/dichloromethane/1% ammonium hydroxide

Sources & evidence

ORD record
ord-d2dfbd7f47584cd8ad600b78831c9a7a
Source dataset
uspto-grants-2013_10
Patent number
US08546410B2

Reaction notes

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