1-(2-Hydroxyethyl)piperazine → 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-[2-(1-piperazinyl)ethoxy]-2(1H)-quinolinone
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[CH:15]=[C:16]([OH:19])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:28].[N:29]1([CH2:35][CH2:36]O)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[CH:15]=[C:16]([O:19][CH2:36][CH2:35][N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:28]Participants
3
Procedure
1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-[2-(1-piperazinyl)ethoxy]-2(1H)-quinolinone was prepared from 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone (INTERMEDIATE 3) and 1-piperazine ethanol by a procedure analogous to that described in EXAMPLE 2. Mass spectrum (ESI) 532.3 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.51 (d, J=8.5 Hz, 2H); 7.36 (t, J=8 Hz, 1H); 7.29 (q, J=6 Hz, 1H); 6.96 (m, 2H); 6.52 (s, 1H); 5.90 (s, 1H); 3.96 (t, J=5.5 Hz, 2H); 2.88 (m, 4H); 2.70 (m, 4H); 2.47 (br, 4H); 2.10 (br, 2H).
Sources & evidence
- ORD record
- ord-608bbcf9f0824cbc859e130076bcd2fd
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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