Benzene, (2-bromoethoxy)- → 3-[4-(2-Phenoxyethyl)piperazin-1-yl]-1-[2-(2,4,5-trifluorophenoxy)ethyl]pyrazin-2(1H)-one, Hydrochloride

HRID 1295722Notes

Reaction equation

HRID 1295722 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([CH2:39][CH2:40][O:41][C:42]3[CH:47]=[C:46](F)[C:45](F)=[CH:44][C:43]=3F)C=CN=2)CCNCC1.C1(OCCBr)C=CC=CC=1>>[ClH:26].[O:41]([CH2:40][CH2:39][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:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 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 1317265263-[4-(2-Phenoxyethyl)piperazin-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 2-bromoethyl phenyl ether (0.22 g, 1.1 mmol). Yield 0.14 g (27%). HPLC purity: 99%. HRMS calc for C24H25F3N4O3 (M)+ 474.1879, found 474.1887.

Sources & evidence

ORD record
ord-6e039fa45a634fc4a843a88994f3e7ad
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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