6-(4-Aminopiperidin-1-yl)pyridine-3-carbonitrile → HCID 53327813, compound

HRID 874954Notes

Reaction equation

HRID 874954 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:4][CH2:3]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>>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:5]2[CH2:6][CH2:7][CH:2]([NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([C:20]4[N:19]=[C:18]([C:17]([F:33])([F:32])[F:16])[O:22][N:21]=4)[CH:24]=3)[CH2:3][CH2:4]2)=[N:9][CH:10]=1)#[N:13]

Participants

3

Reactant 2

HCID 187686716-(4-Aminopiperidin-1-yl)pyridine-3-carbonitrileHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 53327813HCID 53327813, compoundYield 41%

Procedure

This compound was synthesized from 6-(4-aminopiperidin-1-yl)nicotinonitrile and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (70 mg, yield 41%). 1H NMR (400 MHz, CDCl3) δ 8.42 (m, 2H), 8.27 (d, J=7.8 Hz, 1H), 8.04 (d, J=7.8 Hz, 1H), 7.66-7.61 (m, 2H), 6.67 (d, J=9.0 Hz, 1H), 6.14 (d, J=7.8 Hz, 1H), 4.51-4.48 (m, 2H), 4.39-4.29 (m, 1H), 3.20-3.13 (m, 2H), 2.24-2.20 (dd, J=12.3 Hz, 2.3 Hz, 2H), 1.62-1.52 (m, 2H). MS (ESI) m/z: Calculated for C21H17F3N6O2: 442.14. found: 443.2 (M+H)+

Sources & evidence

ORD record
ord-220f8f189b9a43de99b11809a79d5a07
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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