Piperazine → N-[6-Chloro-2-(1-piperazinyl)-5-quinolinyl]-1-cyclohexyl-cyclopropanecarboxamide

HRID 2217822Notes

Reaction equation

[CH:1]1([C:7]2([C:10]([NH:12][C:13]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][C:17](Cl)=[N:18]4)=[O:11])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(#N)C>[Cl:23][C:22]1[C:13]([NH:12][C:10]([C:7]2([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:8][CH2:9]2)=[O:11])=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[CH:16]=[CH:15]2

Participants

Conditions

Temperature: 110 °C

Procedure

To a 10 mL vial was added 1-cyclohexyl-N-(2,6-dichloro-5-quinolinyl)-cyclopropanecarboxamide (Example 26 (b)) (0.13 g), piperazine (0.091 g) and acetonitrile (3 mL). The vial was sealed and heated in a microwave at 110° C. for 40 minutes. The solvent was removed from the cooled reaction and the residue taken up in dichloromethane and purified (SiO2, ammonia:methanol:dichloromethane, 1:2:97 as eluant). The solvent was removed from the combined fractions and the product recrystallised from ethanol to afford the title compound (0.050 g).

Workup

customThe vial was sealed
customThe solvent was removed from the cooled reaction
custompurified (SiO2, ammonia:methanol:dichloromethane, 1:2:97 as eluant)
customThe solvent was removed from the combined fractions
customthe product recrystallised from ethanol

Sources & evidence

ORD record: ord-704737ccb6eb494d81924e14a9bced81
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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