4-Fluorobenzyl bromide → HCID 69219407, compound

HRID 901297Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[NH:8][C:9]2[C:14]([C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[O:23])[CH2:18][CH2:17]1)=[CH:13][N:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:29])[N:8]([CH2:35][C:34]2[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=2)[C:9]2[C:14]([C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)=[O:23])[CH2:18][CH2:17]1)=[CH:13][N:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 680214-Fluorobenzyl bromide

HCID 59699584HCID 59699584, compound

Product 1

HCID 69219407HCID 69219407, compound

Procedure

This compound was prepared from 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridin-3-carboxylic acid ethyl ester (121) and 4-fluorobenzyl bromide according to General Procedure B. Yield 210 mg (55%), MP 132° C.; 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.2 Hz, 3H), 3.21 (m, 4H), 3.91 (m, 4H), 4.31 (q, J=7.2 Hz, 2H), 5.41 (s, 2H), 7.13-7.29 (m, 5H), 7.41 (d, J=6.0 Hz, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.80 (dd, J=4.8, 1.2 Hz, 1H), 8.57 (d, J=6.0 Hz, 1H), 9.09 (s, 1H); EIMS: 521 (M+1). Anal. (C27H25FN4O4S) C, H, N.

Sources & evidence

ORD record: ord-2c0f1e3dccd442d0981a6ab99d157bbf
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361760B2

Reaction notes

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