Bis(2-Methoxyethyl)amine → HCID 10438563, compound

HRID 1785121Notes

Reaction equation

HRID 1785121 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][O:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][O:42][CH3:43]>COCCO>[CH3:35][O:36][CH2:37][CH2:38][N:39]([CH2:40][CH2:41][O:42][CH3:43])[CH2:33][CH2:32][CH2:31][O:30][C:24]1[CH:23]=[C:22]2[C:27]([C:18]([NH:17][C:3]3[C:4]4[O:8][CH2:7][O:6][C:5]=4[C:9]([C:11]#[C:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][C:2]=3[Cl:1])=[N:19][CH:20]=[N:21]2)=[CH:26][C:25]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 2383Bis(2-Methoxyethyl)amineHCID 68882290HCID 68882290, compound

Product 1

HCID 10438563HCID 10438563, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

This was prepared using 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 bis(2-methoxyethyl)amine (264 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 (147 mg, 66%) as a pale brown solid; NMR Spectrum:(DMSOd6) 1.91 (quintet, 2H), 2.65 (m, 6H), 2.72 (t, 2), 3.21 (s, 6H), 3.30 (s, 3H), 3.38 (t, 4H), 3.53 (t, 2H), 3.94 (s, 3H), 4.19 (t, 2H), 6.14 (s, 2H), 7.07 (s, 1H), 7.17 (s, 1H), 7.81 (s, 1H), 8.32 (s, 1H), 9.49 (s, 1H); Mass Spectrum: M+H+ 601/603.

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-4b8ef117e3524324a8958ace0a4d1733
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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