Piperazine → 2-{7-bromo-2-(piperazin-1-yl)-5H-pyrimido-[5,4-b]indol-4-yloxy}ethanol

HRID 1182847Notes

Reaction equation

HRID 1182847 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13](Cl)[N:12]=[C:11]([O:16][CH2:17][CH2:18][OH:19])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C1(C)C=C(C)C=C(C)C=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[N:12]=[C:11]([O:16][CH2:17][CH2:18][OH:19])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 581185092-(7-bromo-2-chloro-5H-pyrimido[5,4-b]indol-4-yloxy)ethanol

Product 1

HCID 581185722-{7-bromo-2-(piperazin-1-yl)-5H-pyrimido-[5,4-b]indol-4-yloxy}ethanol

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

400 mg (1.17 mmol) 2-(7-bromo-2-chloro-5H-pyrimido[5,4-b]indol-4-yloxy)ethanol and 1.0 g (11.7 mmol) piperazine in 50 ml mesitylene were heated to 150° C. for 5 h. Then, the solvent was removed and the residue was taken up in EtOH and filtrated. Having removed the solvent, 250 mg (55%) of the title substance was obtained. ESI-MS [m/z]: 392, 394[M+H]+

Workup

  1. customThen, the solvent was removed
  2. filtrationfiltrated
  3. customHaving removed the solvent, 250 mg (55%) of the title substance
  4. customwas obtained

Sources & evidence

ORD record
ord-47bb2a1ead9046bcba86bcfb690cced5
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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