3-Fluorobenzyl bromide → HCID 59699639, compound

HRID 901268Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:30])[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][C:12]([Cl:29])=[CH:11][N:10]=2)=[O:5])[CH3:2].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35]Br>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:30])[N:8]([CH2:35][C:34]2[CH:37]=[CH:38][CH:39]=[C:32]([F:31])[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][C:12]([Cl:29])=[CH:11][N:10]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 680073-Fluorobenzyl bromide

HCID 69216352HCID 69216352, compound

Product 1

HCID 59699639HCID 59699639, compound

Procedure

This compound was prepared from 6-fluoro-6-chloro-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (82) and 3-fluorobenzyl bromide according to General Procedure B. Yield 207 mg (37%), MP 186° C.; 1H-NMR (DMSO-d6): δ 1.28 (t, J=7.2 Hz, 3H), 3.16 (m, 4H), 3.92 (m, 4H), 4.32 (q, J=7.2 Hz, 2H), 5.24 (s, 2H), 7.07 (m, 3H), 7.15 (dd, J=3.6, 5.2 Hz, 1H), 7.30 (m, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 8.29 (d, J=2.8 Hz, 1H), 8.73 (d, J=2.8 Hz, 1H); EIMS: 555 (M+1). Anal. (C27H24ClFN4O4S) C, H, N.

Sources & evidence

ORD record: ord-bb09ce11c2784daab3f60b088d92c89b
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361760B2

Reaction notes

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