Benzyl Bromide → 3-(4-Benzylpiperazin-1-yl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]pyrazin-2(1H)-one hydrochloride

HRID 1295724Notes

Reaction equation

HRID 1295724 reaction equation
[N:1]1([C:7]2[C:8](=[O:25])[N:9]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=3[F:24])[CH:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[ClH:26].N1(C2C(=O)N(CCOC3C=C(F)C(F)=CC=3F)C=CN=2)CCNCC1.[CH2:52](Br)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>>[ClH:26].[CH2:52]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:8](=[O:25])[N:9]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=3[F:24])[CH:10]=[CH:11][N:12]=2)[CH2:2][CH2:3]1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 104058482(1H)-Pyrazinone, 3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-HCID 116397093-(1-Piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone, Hydrochloride

Product 1

HCID 104353023-(4-Benzylpiperazin-1-yl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]pyrazin-2(1H)-one hydrochloride

Procedure

The title compound was prepared according to the procedure of Example 60 starting from 3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone (0.35 g, 1.0 mmol; from the free base of Example 3) and benzyl bromide (0.19 g, 1.1 mmol) Yield: 0.17 g (35%); HPLC purity: 99%; mp 214-214.5° C. HRMS calc for C23H23F3N4O2 (M)+ 444.1773, found 444.1789.

Sources & evidence

ORD record
ord-33b9381be5ad40ca9f2e1fe044a466b6
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

Loading…