Benzyl Bromide → 1-Benzyl-6-chloro-4-[4-(furan-2-carbonyl)-piperazin 1-yl]-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901289Notes

Reaction equation

HRID 901289 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]#[N:14])=[C:5]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)=[O:22])[CH2:17][CH2:16]1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][N:10]=2)[C:5]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:17][CH2:16]2)=[C:6]([C:13]#[N:14])[C:7]1=[O:12])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 692157666-Chloro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 596996071-Benzyl-6-chloro-4-[4-(furan-2-carbonyl)-piperazin 1-yl]-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Procedure

This compound was prepared from 6-chloro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (101) and benzyl bromide according to General Procedure B. Yield 223 mg (31%), MP 196° C.; 1H-NMR (DMSO-d6): δ 3.75 (m, 4H), 3.94 (m, 4H), 5.51 (s, 2H), 6.66 (dd, J=1.6, 3.6 Hz, 1H), 7.09 (d, J=3.2 Hz, 1H), 7.22-7.28 (m, 5H), 7.89 (d, J=1.6 Hz, 1H), 8.32 (d, J=2.4 Hz, 1H), 8.76 (d, J=2.4 Hz, 1H); EIMS: 474 (M+1). Anal. (C25H20ClN5O3) C, H, N.

Sources & evidence

ORD record
ord-e569bb3296ff42e3b159e0f3c7f809c2
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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