HCID 22284867, compound → HCID 131725196, compound

HRID 1061515Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:24]#[N:25].Cl.[CH3:27][CH:28]([O:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[O:39])=[CH:33][CH:32]=1)[CH3:29]>CN(C=O)C>[C:24]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[N:43]1[CH2:42][CH2:41][N:40]([C:38]([NH:37][C:34]3[CH:35]=[CH:36][C:31]([O:30][CH:28]([CH3:29])[CH3:27])=[CH:32][CH:33]=3)=[O:39])[CH2:45][CH2:44]1)=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1)[CH:7]=2)#[N:25]

Participants

Conditions

Temperature: 40 °C

Procedure

To the DMF solution (3 mL) of the 4-chloroquinoline (0.175 g, 0.487 mmol) from step A added K2CO3 (0.155 g, 1.10 mmol) followed by N-[4-(methylethoxy)phenyl]piperazinylcarboxamide hydrochloride (0.169 g, 0.535 mmol). The reaction mixture was heated to 40° C. overnight, during that period starting materials were consumed. After cooling diluted with EtOAc/water and the layers were separated. The organic layer was dried, filtered and evaporated to afford desired product as a crude residue. The crude residue was purified by RP-HPLC to afford {4-[3-cyano-6-methoxy-7-(3-piperidylpropoxy)quinolin-4-yl)piperazinyl}-N-[4-(methylethoxy)phenyl]carboxamide as the desired product (0.195 g, 69%). MS(ES) 587.3 (M+H)

Workup

customwere consumed
temperatureAfter cooling
additiondiluted with EtOAc/water
customthe layers were separated
customThe organic layer was dried
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-0ac1ec933e5b4e98889b81b56f6f65ea
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960580B2

Reaction notes

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