4-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanal → 7-{4-[4-(6,7,8,9-Tetrahydro-5H-benzocyclohepten-1-yl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373546Notes

Reaction equation

HRID 1373546 reaction equation
[C:1]1([NH2:12])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[O:13]=[C:14]1[NH:23][C:22]2[N:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH:28]=O)[CH:19]=[CH:18][C:17]=2[CH2:16][CH2:15]1>>[C:1]1([N:12]2[CH2:17][CH2:22][N:21]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:20]3[N:21]=[C:22]4[C:17]([CH2:16][CH2:15][C:14](=[O:13])[NH:23]4)=[CH:18][CH:19]=3)[CH2:20][CH2:19]2)[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 210733774-((7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)oxy)butanalHCID 21701862HCID 21701862, compound

Product 1

HCID 210737197-{4-[4-(6,7,8,9-Tetrahydro-5H-benzocyclohepten-1-yl)-piperazin-1-yl]-butoxy}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

Procedure

In a manner similar to that of other examples above, 6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamine (0.178 g) was coupled by reductive amination to 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde followed by typical workup and purification to give the title compound as the hydrochloride salt (0.109 g). MS: APCI: M+1: 449.3 (Exact Mass: 448.26).

Workup

  1. customfollowed by typical workup and purification

Sources & evidence

ORD record
ord-53a44c34cedc457a905657033e0c3dfd
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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