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

HRID 2217829Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14](OS(C)(=O)=O)[CH2:13]1)[CH:6]=[CH:5]2.[CH3:32][NH2:33]>C(O)C>[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@@H:14]([NH:33][CH3:32])[CH2:13]1)[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a 10 mL vial was added N-[6-Chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 33(a)) (225 mg) and 8M methylamine in ethanol (6 mL). The vial was sealed and heated at 80° C. for 120 minutes within a microwave. The solvent was removed under vacuum and purified (SiO2, ammonia:methanol:dichloromethane, 1:2:97 as eluant) to afford the titled compound (0.033 g).

Workup

customThe vial was sealed
customThe solvent was removed under vacuum
custompurified (SiO2, ammonia:methanol:dichloromethane, 1:2:97 as eluant)

Sources & evidence

ORD record: ord-4f1e934f0d944a38b5eb091b9701b196
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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