Piperazine → HCID 22291691, compound

HRID 457321Notes

Reaction equation

HRID 457321 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:31]([Cl:34])=[CH:32][N:33]=1)[C:5]([NH:7][C:8]1[CH:30]=[CH:29][C:11]2[CH2:12][CH2:13][C:14]3[C:15]([C:26]([NH2:28])=[O:27])=[N:16][N:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:18]=3[C:10]=2[CH:9]=1)=[O:6].[NH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>CCO>[Cl:34][C:31]1[C:4]([C:5]([NH:7][C:8]2[CH:30]=[CH:29][C:11]3[CH2:12][CH2:13][C:14]4[C:15]([C:26]([NH2:28])=[O:27])=[N:16][N:17]([C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=5)[C:18]=4[C:10]=3[CH:9]=2)=[O:6])=[CH:3][C:2]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[N:33][CH:32]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 22291629HCID 22291629, compound

Product 1

HCID 22291691HCID 22291691, compoundYield 53%

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 248 (1 g, 0.0020 mol) and piperazine (3.44 g, 0.040 mol) in 5 mL of EtOH. The reaction was run at 100° C. for 24 h. The off-white precipitate that formed in the crude reaction mixture was filtered and washed with EtOH to afford 0.579 g of title compound (yield: 53%). 1H NMR (300 MHz, d6-DMSO): 2.67 (t, 4H, J=4.9 Hz), 2.85–2.90 (m, 4H), 3.36 (t, 4H, J=4.9 Hz), 6.80 (s, 1H), 7.18–7.19 (m, 1H), 7.25 (s, 1H), 7.27–7.35 (m, 3H), 7.37–7.39 (dd, 1H, J=8 Hz, 2 Hz), 7.51–7.55 (m, 3H), 8.09 (s, 1H), 10.28 (s, 1H). M=1=547

Workup

  1. customThe off-white precipitate that formed in the crude
  2. customreaction mixture
  3. filtrationwas filtered
  4. washwashed with EtOH

Sources & evidence

ORD record
ord-16774b9e48d9471bbf6e4bf189b72742
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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