Piperazine → HCID 22291750, compound

HRID 457308Notes

Reaction equation

HRID 457308 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23][C:24](=[O:33])[C:25]6[C:30]([Cl:31])=[CH:29][N:28]=[C:27](Cl)[CH:26]=6)[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:34]([NH2:36])=[O:35])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CCO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23][C:24](=[O:33])[C:25]6[C:30]([Cl:31])=[CH:29][N:28]=[C:27]([N:37]7[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]7)[CH:26]=6)[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:34]([NH2:36])=[O:35])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 22291587HCID 22291587, compound

Product 1

HCID 22291750HCID 22291750, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by the same procedure as in Example 214 starting with the title compound of Example 211 (1 g, 0.0018 mol) and piperazine (3 g, 0.036 mol) in EtOH (4 mL). The reaction was run at 95° C. for 24 h. After allowing the reaction mixture to cool down, the volatiles were removed under vacuum. The residue was triturated with H2O and finally with EtOH to yield 0.572 g of the title compound (yield: 55%). 1H NMR (300 MHz, d6-DMSO): δ 2.71 (s, broad, 4H), 2.86–3.30 (m, 4H), 3.39 (s, broad, 4H), 6.07 (s, 2H), 6.85 (s, 1H), 6.93–6.95 (dd, 1H, J=8.2 Hz, 1.9 Hz), 7.00 (d, 1H, J=8.2 Hz), 7.09 (d, 1H, J=1.9 Hz), 7.24–7.30 (m, 3H), 7.38–7.41 (dd, 1H, J=8.2 Hz, 1.74 Hz), 7.49 (s, 1H), 8.12 (s, 1H), 10.32 (s, 1H). M+1=573.

Workup

  1. temperatureto cool down
  2. customthe volatiles were removed under vacuum
  3. customThe residue was triturated with H2O and finally with EtOH

Sources & evidence

ORD record
ord-45ce4aeff2654ba99144cb11dd7800af
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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