3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → Methyl 4-(5-cyanopyridin-2-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazine-2-carboxylate

HRID 874933Notes

Reaction equation

HRID 874933 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[N:7][CH:8]=1)#[N:2].[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]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[C:26]([C:23]4[N:22]=[C:21]([C:20]([F:36])([F:35])[F:19])[O:25][N:24]=4)[CH:27]=3)[CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[N:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67323895Methyl 4-(5-cyanopyridin-2-yl)piperazine-2-carboxylate

Product 1

HCID 67325316Methyl 4-(5-cyanopyridin-2-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazine-2-carboxylateYield 73%

Procedure

This compound was synthesized from methyl 4-(5-cyanopyridin-2-yl)piperazine-2-carboxylate and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (130 mg, yield 73%). 1H NMR (400 MHz, CDCl3) δ 8.55-8.50 (m, 1H), 8.42 (br s, 1H), 8.24 (m, 1H), 7.73-7.64 (m, 3H), 6.71 (d, J=9.0 Hz, 1H), 4.94 (m, 1H), 4.52-4.41 (m, 1H), 3.78 (s, 3H), 3.75 (m, 2H), 3.69-3.59 (m, 1H), 3.51-3.48 (m, 1H), 3.11-3.04 (m, 1H). MS (ESI) m/z: Calculated for C22H17F3N6O4: 486.13. found: 487.2 (M+H)+.

Sources & evidence

ORD record
ord-e05582c252b54e09a2f00094c008001c
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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