1-Methylpiperazine → HCID 68884140, compound

HRID 1785157Notes

Reaction equation

HRID 1785157 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:15][C:16]3[C:24]4[O:23][CH2:22][O:21][C:20]=4[C:19]([C:25]#[C:26][CH2:27][O:28][CH3:29])=[CH:18][C:17]=3[Cl:30])=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:31][CH3:32].[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>>[Cl:30][C:17]1[CH:18]=[C:19]([C:25]#[C:26][CH2:27][O:28][CH3:29])[C:20]2[O:21][CH2:22][O:23][C:24]=2[C:16]=1[NH:15][C:9]1[C:8]2[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:37]3[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]3)=[C:6]([O:31][CH3:32])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 68880474HCID 68880474, compound

Product 1

HCID 68884140HCID 68884140, compoundYield 17%

Procedure

7-(2-Chloroethoxy)-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine (0.2 g, 0.4 mmol) was dissolved in 1-methylpiperazine (4 ml) and heated at 50 C for 12 hours. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography on alumina eluting with a mixture of 0-10%, methanol in dichloromethane to give the product as a white solid (0.037 g, 17%). NMR Spectrum: (CDCl3) 2.28 (s, 3H), 2.50 (s(broad), 4H), 2.63 (s(broad), 4H), 2.94 (t, 2H), 3.44 (s, 3H), 4.01 (s, 3H), 4.33 (t, 2H), 4.36 (s, 2H), 6.08 (s, 2H), 6.78 (s, 1H), 7.04 (s, 1H), 7.05 (s, 1H), 7.25 (s, 1H), 8.63 (s, 1H). Mass Spectrum: M+H+ 540 and M+H−]538.

Workup

  1. temperatureheated at 50 C for 12 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue purified by flash chromatography on alumina eluting with a mixture of 0-10%, methanol in dichloromethane

Sources & evidence

ORD record
ord-e7ff0015a9634254bfe73bb5c5b0b878
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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