Ammonia → 3-(3,4-Difluorophenyl)-5-(pyridin-3-yl)-1,2,4-oxadiazole

HRID 713787Notes

Reaction equation

HRID 713787 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5](=[N:7][OH:8])[NH2:6].Cl.[C:14](Cl)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.N>>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:14]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 40943713,4-difluoro-N'-hydroxybenzenecarboximidamide

Product 1

HCID 670260323-(3,4-Difluorophenyl)-5-(pyridin-3-yl)-1,2,4-oxadiazole

Procedure

The title compound was prepared according to the procedure of Example 1 using 3,4-difluoro-N′-hydroxybenzimidamide (Tyger Scientific) and nicotinoyl chloride hydrochloride (Aldrich). 1H NMR (300 MHz, DMSO-d6) δ 7.74 (dd, J=7.5, 4.4 Hz, 1H), 8.60 (dt, J=7.8, 2.1 Hz, 1H), 8.93 (dd, J=4.8, 1.6 Hz, 1H), 9.38 (dd, J=2.2, 1.0 Hz, 1H), 9.44-9.48 (m, 3H) ppm; MS (DCl/NH3) m/z 260 (M+H)+.

Sources & evidence

ORD record
ord-a655f498e0b140449c2dcad2fa7e0202
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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