Ethanolamine → N-[6-Chloro-2-[3-[(2-hydroxyethyl)amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217885Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:23][C:24](=[O:32])[CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)[CH:6]=[CH:5]2.[NH2:33][CH2:34][CH2:35][OH:36]>C(#N)C>[Cl:1][C:2]1[C:3]([NH:23][C:24](=[O:32])[CH2:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:33][CH2:34][CH2:35][OH:36])[CH2:13]1)[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

N-[6-Chloro-2-[(3R)-3-[(methylsulfonyl)oxy]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 80(a)) (0.2 g), 2-amino-ethanol (0.075 ml) and acetonitrile (3 ml) were loaded into a 10 ml microwave reaction vial, capped and heated at 80° C. for 90 minutes within a single mode microwave. The solvent was removed under vacuum and the residue was purified by chromatography (SiO2, 7M ammonia in methanol:dichloromethane 1:99 as eluant) to give the title compound as a solid (0.018 g).

Workup

customcapped
customThe solvent was removed under vacuum
customthe residue was purified by chromatography (SiO2, 7M ammonia in methanol:dichloromethane 1:99 as eluant)

Sources & evidence

ORD record: ord-e3a804599372496f9c065728b7099f7b
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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