1-(2-Chloro-3-piperazin-1-yl-phenyl)-ethanone trifluoroacetate → 7-{4-[4-(3-Acetyl-2-chloro-phenyl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one

HRID 1373559Notes

Reaction equation

HRID 1373559 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:14]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21](=[O:23])[CH3:22].[O:24]=[C:25]1[NH:34][C:33]2[N:32]=[C:31]([O:35][CH2:36][CH2:37][CH2:38][CH:39]=O)[CH:30]=[CH:29][C:28]=2[CH:27]=[CH:26]1>>[C:21]([C:10]1[C:9]([Cl:8])=[C:14]([N:15]2[CH2:20][CH2:19][N:18]([CH2:39][CH2:38][CH2:37][CH2:36][O:35][C:31]3[N:32]=[C:33]4[C:28]([CH:27]=[CH:26][C:25](=[O:24])[NH:34]4)=[CH:29][CH:30]=3)[CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 210731381-(2-Chloro-3-piperazin-1-yl-phenyl)-ethanone trifluoroacetateHCID 210733804-(7-Oxo-7,8-dihydro-1,8-naphthyridin-2-yloxy)butanal

Product 1

HCID 210736487-{4-[4-(3-Acetyl-2-chloro-phenyl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one

Procedure

In a manner similar to that of other examples above, 1-(2-chloro-3-piperazin-1-yl-phenyl)-ethanone trifluoroacetate 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, mp 108–110° C. MS: APCI: M+1: 455.2 (Exact Mass: 454.18).

Workup

  1. customfollowed by typical workup and purification

Sources & evidence

ORD record
ord-f27b2e2cea7f42c49310decc16ac5fe2
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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