1-Biphenyl-3-yl-piperazine → (4-([1,1'-Biphenyl]-3-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanone

HRID 875016Notes

Reaction equation

HRID 875016 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:2]=1.[F:19][C:20]([F:36])([F:35])[C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29](O)=[O:30])[N:22]=1>>[C:1]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:8][CH2:9][N:10]([C:29]([C:28]3[CH:32]=[CH:33][CH:34]=[C:26]([C:23]4[N:22]=[C:21]([C:20]([F:35])([F:19])[F:36])[O:25][N:24]=4)[CH:27]=3)=[O:30])[CH2:11][CH2:12]2)[CH:2]=1

Participants

3

Reactant 2

HCID 27567121-Biphenyl-3-yl-piperazineHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 53327926(4-([1,1'-Biphenyl]-3-yl)piperazin-1-yl)(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)methanoneYield 40%

Procedure

This compound was synthesized from 1-([1,1′-biphenyl]-3-yl)piperazine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (110 mg, yield 40%). 1H NMR (400 MHz, MeOD) δ 8.27-8.25 (m, 1H), 8.22-8.21 (m, 1H), 7.75-7.70 (m, 2H), 7.60-7.58 (m, 2H), 7.43-7.40 (m, 2H), 7.53-7.30 (m, 2H), 7.22-7.21 (m, 1H), 7.14-7.12 (m, 1H), 7.02-6.00 (m, 1H), 3.99 (m, 2H), 3.67 (m, 2H), 3.37 (m, 2H), 3.24 (m, 2H). MS (ESI) m/z: Calculated for C26H21F3N4O2: 478.16. found: 479.1 (M+H)+

Sources & evidence

ORD record
ord-fe8d7bb76ff147a385b1123e27d5df1f
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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