HCID 22284867, compound → HCID 10189509, compound

HRID 1061516Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH2:20][CH2:21][CH2:22]C1CCCNC1)[CH:10]=2)=[O:5])[CH3:2].Cl.[CH3:30][CH:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[O:42])=[CH:36][CH:35]=1)[CH3:32]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[N:46]1[CH2:45][CH2:44][N:43]([C:41](=[O:42])[NH:40][C:37]3[CH:38]=[CH:39][C:34]([O:33][CH:31]([CH3:30])[CH3:32])=[CH:35][CH:36]=3)[CH2:48][CH2:47]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH2:20][CH2:21][CH2:22][N:8]1[CH2:9][CH2:14][CH2:15][CH2:6][CH2:7]1)[CH:10]=2)=[O:5])[CH3:2]

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-{4-(4-Isopropoxy-phenylcarbamoyl)piperazin-1-yl]-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinolin-3-carboxylic acid ethyl ester (0.170 g, 50%). MS(ES) 634 (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-9732d0de291340239b7e7d3eeb277127
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960580B2

Reaction notes

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