2-piperazin-1-yl-1H-benzoimidazole → (4-(1H-Benzo[d]imidazol-2-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanone

HRID 874993Notes

Reaction equation

HRID 874993 reaction equation
[N:1]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[N:19]=1>>[NH:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[N:1]1[CH2:6][CH2:5][N:4]([C:26]([C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:20]3[N:19]=[C:18]([C:17]([F:32])([F:16])[F:33])[O:22][N:21]=3)[CH:24]=2)=[O:27])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 27371932-piperazin-1-yl-1H-benzoimidazoleHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 53327885(4-(1H-Benzo[d]imidazol-2-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanoneYield 23%

Procedure

This compound was synthesized from 2-(piperazin-1-yl)-1H-benzo[d]imidazole and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (100 mg, yield 23%). 1H NMR (400 MHz, DMSO-d6) δ 11.49 (br s, 1H), 8.19-8.17 (d, J=8.5 Hz, 1H), 8.11 (s, 1H), 7.76-7.72 (m, 2H), 7.21 (m, 2H), 6.94 (m, 2H), 3.80 (m, 2H), 3.63-3.52 (m, 6H). MS (ESI) m/z: Calculated for C21H17F3N6O2: 442.14. found: 441.4 (M−H)−

Sources & evidence

ORD record
ord-aca9a91e3f924f0991c1608f7f7dec7d
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…