3-Fluorobenzyl bromide → 6-Chloro-1-(3-fluorobenzyl)-2-oxo-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901290Notes

Reaction equation

HRID 901290 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.[F:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([F:28])[CH:30]=1)[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

Participants

3

Reactant 2

HCID 680073-Fluorobenzyl bromideHCID 692157666-Chloro-2-oxo-4-[4-(furan-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 596996096-Chloro-1-(3-fluorobenzyl)-2-oxo-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-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 3-fluorobenzyl bromide according to General Procedure B. Yield 113 mg (15%), MP 134° C.; 1H-NMR (DMSO-d6): δ 3.75 (m, 4H), 3.95 (m, 4H), 5.51 (s, 2H), 6.66 (dd, J=1.6, 3.2, Hz, 1H), 7.06-7.10 (m, 4H), 7.33 (m, 1H), 7.89 (d, J=2.0 Hz, 1H), 8.33 (dd, J=2.4 Hz, 1H), 8.75 (d, J=2.4 Hz, 1H); EIMS: 492 (M+1). Anal. (C25H19ClFN5O3) C, H, N.

Sources & evidence

ORD record
ord-323c6728473d456ca795aee31b1e4769
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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