Ammonia → 3-(pyridin-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,2,4-oxadiazole

HRID 450683Notes

Reaction equation

HRID 450683 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]([OH:12])=O)[CH:9]=[C:4]2[CH:3]=[CH:2]1.O[N:14]=[C:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.N>>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]2[N:22]=[C:10]([C:8]3[CH:9]=[C:4]4[CH:3]=[CH:2][NH:1][C:5]4=[N:6][CH:7]=3)[O:12][N:14]=2)[CH:17]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 219070181H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 445449643-(pyridin-3-yl)-5-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,2,4-oxadiazole

Procedure

The title compound was prepared according to Method C using 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (Adesis) and N′-hydroxynicotinimidamide (Tyger). 1H NMR (300 MHz, DMSO-d6) δ 6.71 (d, J=3.4 Hz, 1 H), 7.66 (ddd, J=7.9, 4.8, 0.8 Hz, 1 H), 7.70 (d, J=3.4 Hz, 1 H), 8.47 (dt, J=8.1, 1.9 Hz, 1 H), 8.78-8.86 (m, 2 H), 9.05 (d, J=2.0 Hz, 1 H), 9.28 (dd, J=2.2, 0.8 Hz, 1 H) ppm; MS (DCI/NH3) m/z 264 (M+H)+.

Sources & evidence

ORD record
ord-294ce934fbd94da48c7a203bed97b709
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

Loading…