1-methyl-8-piperazin-1-yl-3,4-dihydro-1H-quinolin-2-one hydrochloride → 7-{4-[4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-8-yl)-piperazin-1-yl]-butoxy}1H-[1,8]naphthyridin-2-one

HRID 1373652Notes

Reaction equation

HRID 1373652 reaction equation
Cl.[CH3:2][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:6][CH2:5][C:4]1=[O:19].[O:20]=[C:21]1[NH:30][C:29]2[N:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34][CH:35]=O)[CH:26]=[CH:25][C:24]=2[CH:23]=[CH:22]1>>[CH3:2][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]2[CH2:18][CH2:17][N:16]([CH2:35][CH2:34][CH2:33][CH2:32][O:31][C:27]3[N:28]=[C:29]4[C:24]([CH:23]=[CH:22][C:21](=[O:20])[NH:30]4)=[CH:25][CH:26]=3)[CH2:15][CH2:14]2)[CH2:6][CH2:5][C:4]1=[O:19]

Participants

3

Reactant 2

HCID 210731991-methyl-8-piperazin-1-yl-3,4-dihydro-1H-quinolin-2-one hydrochlorideHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Product 1

HCID 210734957-{4-[4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-8-yl)-piperazin-1-yl]-butoxy}1H-[1,8]naphthyridin-2-one

Procedure

In a manner similar to that of other examples above, 1-methyl-8-piperazin-1-yl-3,4-dihydro-1H-quinolin-2-one hydrochloride was coupled by reductive amination to 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde followed by typical workup and purification to give the title compound. MS: APCI: M+1: 462.2 (Exact Mass: 461.24).

Workup

  1. customfollowed by typical workup and purification

Sources & evidence

ORD record
ord-9cbd6ee24a5e4d198b816ee47cf67d6e
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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