4-Methoxypiperidine → HCID 68880434, compound

HRID 1785128Notes

Reaction equation

HRID 1785128 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][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>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:40]3[CH2:41][CH2:42][CH:37]([O:36][CH3:35])[CH2:38][CH2:39]3)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 776664-MethoxypiperidineHCID 68882290HCID 68882290, compound

Product 1

HCID 68880434HCID 68880434, compoundYield 80%

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 4-methoxypiperidine (246 mg, 2.14 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanolic ammonia in dichloromethane as eluent. There was thus obtained the title compound (184 mg, 80%) as a pale yellow solid; NMR Spectrum:(CDCl3) 1.55-1.70 (m, 2H), 1.85-2.00 (m, 2H), 2.10 (quintet, 2H), 2.24 (m, 2H), 2.56 (t, 2H), 2.72 (t, 2), 2.78 (m, 2H), 3.24 (m, 1H), 3.34 (s, 3H), 3.42 (s, 3H), 3.62 (t, 2H), 3.98 (s, 3H), 4.24 (t, 2H), 6.05 (s, 2H), 6.90 (s, 1H), 7.04 (s, 1H), 7.09 (s, 1H), 7.28 (s, 1H), 8.61 (s, 1H); Mass Spectrum: M+H+ 583/585.

Workup

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

Sources & evidence

ORD record
ord-8f8cfe34e4c84f5096edd5b2bb9fa917
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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