1-{4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazin-1-yl}-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone → 6-Fluoro-2-methyl-3-[2-(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]benzonitrile

HRID 2173453Notes

Reaction equation

HRID 2173453 reaction equation
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([CH2:11][CH:12]=O)=[CH:4][CH:3]=1.Cl.[N:15]1([C:21](=[O:34])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH:33]=[N:32][N:31]=[N:30]3)=[CH:25][CH:24]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.N1ON=C2C=C(CCN3CCN(C(=O)CC4C=CC(N5C=NN=N5)=CC=4)CC3)C=CC=12>>[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([CH2:11][CH2:12][N:18]2[CH2:17][CH2:16][N:15]([C:21](=[O:34])[CH2:22][C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH:33]=[N:32][N:31]=[N:30]4)=[CH:27][CH:28]=3)[CH2:20][CH2:19]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 573312411-{4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazin-1-yl}-2-[4-(1H-tetrazol-1-yl)phenyl]ethanoneHCID 675172361-(piperazin-1-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone hydrochlorideHCID 866930416-Fluoro-2-methyl-3-(2-oxoethyl)benzonitrile

Product 1

HCID 675182646-Fluoro-2-methyl-3-[2-(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]benzonitrile

Procedure

6-Fluoro-2-methyl-3-[2-(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]benzonitrile was prepared from 6-fluoro-2-methyl-3-(2-oxoethyl)benzonitrile and 1-(piperazin-1-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone hydrochloride in an analogous fashion to that described for 1-{4-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]piperazin-1-yl}-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone (General Method C). 1H-NMR (400 MHz, CD3OD) δ 9.89 (s, 1H), 7.76˜7.78 (m, 2H), 7.51˜7.55 (m, 1H), 7.40˜7.42 (m, 2H), 7.21˜7.25 (m, 1H), 4.44˜4.45 (m, 1H), 4.16˜4.17 (m, 1H), 3.84 (s, 2H), 3.38˜3.56 (m, 2H), 2.98˜3.01 (m, 4H).

Sources & evidence

ORD record
ord-ecc7a82bee014b729240f823c3179a16
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…