1-Methylpiperazin-2-one → HCID 10257666, compound

HRID 1785130Notes

Reaction equation

HRID 1785130 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][CH2:14][O:15][CH3:16])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][CH2:32][CH2:33]Cl)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][C:37]1=[O:42]>COCCO>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][CH2:14][O:15][CH3:16])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][CH2:32][CH2:33][N:39]3[CH2:40][CH2:41][N:36]([CH3:35])[C:37](=[O:42])[CH2:38]3)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 43990421-Methylpiperazin-2-oneHCID 68882290HCID 68882290, compound

Product 1

HCID 10257666HCID 10257666, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

This was prepared by the method described in example 13 using N-[5-Chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (200 mg, 0.40 mmol) and 1-methylpiperazin-2-one (226 mg, 1.98 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent. There was thus obtained the title compound (166 mg, 72%) as a pale brown solid; NMR Spectrum:(CDCl3) 2.10 (quintet, 2H), 2.61 (t,2H), 2.72 (m, 4H), 2.95 (s, 3H), 3.15 (s, 2H), 3.31 (t, 2H), 3.40 (s, 3H), 3.61 (t, 2H), 3.98 (s, 3H), 4.25 (t, 2H), 6.06 (s, 2H), 6.96 (s, 1H), 7.03 (s, 1H), 7.12 (s, 1H), 7.26 (s, 1H), 8.60 (s, 1H); Mass Spectrum: M+H+ 582/584.

Workup

  1. customThis was prepared by the method
  2. customThe crude product was purified by column chromatography on silica using
  3. temperatureincreasing concentrations of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-343f7a7d141f4104bcc5e97ba57373f9
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

Loading…