4-Piperidinemethanol → HCID 10325954, compound

HRID 1785110Notes

Reaction equation

HRID 1785110 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.[NH:35]1[CH2:40][CH2:39][CH:38]([CH2:41][OH:42])[CH2:37][CH2:36]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:35]3[CH2:40][CH2:39][CH:38]([CH2:41][OH:42])[CH2:37][CH2:36]3)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 4207714-PiperidinemethanolHCID 68882290HCID 68882290, compound

Product 1

HCID 10325954HCID 10325954, 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 (192 mg, 0.38 mmol) and 4-piperidinemethanol (220 mg, 1.9 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 (177 mg, 80%) as a pale yellow solid; NMR Spectrum:(DMSOd6) 1.10-1.20 (m, 2H), 1.35 (m, 1H), 1.64 (d, 2H), 1.88 (t, 2H), 1.95 (quintet, 2H), 2.45 (t, 2H), 2.72 (t, 2H), 2.89 (d, 2H), 3.26 (t, 2H), 3.32 (s, 3H), 3.53 (t, 2H), 3.94 (s, 3H), 4.18 (t, 2H), 4.37 (t, 1H), 6.14 (s, 2H), 7.07 (s, 1H), 7.17 (s, 1H), 7.82 (s, 1H), 8.32 (s, 1H), 9.48 (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-8cc1be49569b4380ba972522b23e8531
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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