Ammonia → 5-(Imidazo[1,5-a]pyridin-6-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

HRID 578166Notes

Reaction equation

HRID 578166 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=12.O[N:14]=[C:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.N>>[CH:2]1[N:1]=[CH:5][N:4]2[CH:9]=[C:8]([C:10]3[O:12][N:22]=[C:15]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[N:14]=3)[CH:7]=[CH:6][C:3]=12

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 7075376Imidazo(1,2-a)pyridine-6-carboxylic acid

Product 1

HCID 445448685-(Imidazo[1,5-a]pyridin-6-yl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

Procedure

The title compound was prepared according to Method C using imidazo[1,2-a]pyridine-6-carboxylic acid (Maybridge) and N′-hydroxynicotinimidamide (Tyger). 1H NMR (300 MHz, DMSO-d6) δ 7.67 (ddd, J=8.1, 4.8, 1.0 Hz, 1H), 7.76 (d, J=1.4 Hz, 1H), 7.78-7.92 (m, 2H), 8.21 (s, 1H), 8.46 (dt, J=8.2, 1.8 Hz, 1H), 8.83 (dd, J=4.7, 1.7 Hz, 1H), 9.27 (dd, J=2.2, 0.8 Hz, 1H), 9.69 (dd, J=1.7, 1.0 Hz, 1H) ppm; MS (DCI/NH3) m/z 264 (M+H)+.

Sources & evidence

ORD record
ord-c337ffe2c70b41ee82dc417ac9602985
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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