1-Methylpiperazin-2-one → 4-{3-[(4-{[5-Chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]amino}-6-methoxyquinazolin-7-yl)oxy]propyl}-1-methylpiperazin-2-one

HRID 1785136Notes

Reaction equation

HRID 1785136 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][O:14][CH3:15])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32]Cl)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][C:36]1=[O:41]>COCCO>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][O:14][CH3:15])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:38]3[CH2:39][CH2:40][N:35]([CH3:34])[C:36](=[O:41])[CH2:37]3)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 43990421-Methylpiperazin-2-oneHCID 68882624N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine

Product 1

HCID 100537054-{3-[(4-{[5-Chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]amino}-6-methoxyquinazolin-7-yl)oxy]propyl}-1-methylpiperazin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

This was prepared using the method described in example 13 using N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (250 mg, 0.51 mmol) and 1-methylpiperazin-2-one (290 mg, 2.54 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 (229 mg, 79%) as a pale brown solid; NMR Spectrum: ()MSOd6) 1.98 (quintet, 2H), 2.56 (t, 2H), 2.69 (t, 2H), 2.82 (s, 3H), 3.01 (s, 2H), 3.30 (t, 2H), 3.35 (s, 3H), 3.93 (s, 3H), 4.19 (t, 2H), 4.37 (s, 2H), 6.16 (s, 2H), 7.15 (s, 1H), 7.18 (s, 1H), 7.81 (s, 1H), 8.32 (s, 1H), 9.52 (s, 1H); Mass Spectrum: M+H+ 566/568.

Workup

  1. customThis was prepared
  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-6455698656014bb88efa06f83549a201
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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