Methylamine → N-[6-Chloro-2-[3-(methylamino)-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217886Notes

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.[CH3:33][NH2:34]>C(O)C>[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][CH:14]([NH:34][CH3:33])[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) and 8M methylamine in ethanol (5 ml) were placed into a 10 ml microwave vial and heated at 80° C. for 60 minutes within a single mode microwave. The reaction was pre-absorbed onto silica and purified (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:3:96 as eluant). The resulting product was recrystallised from acetonitrile to afford the title compound (0.007 g).

Workup

customThe reaction was pre-absorbed onto silica
custompurified (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:3:96 as eluant)
customThe resulting product was recrystallised from acetonitrile

Sources & evidence

ORD record: ord-aafeb68919a643ffa21b928fb5e74ade
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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