Hydroxyamine hydrochloride → N-hydroxy-3-((2-phenylimidazo[1,2-a]pyridin-3-yl)-methyl)-1,2,4-oxadiazole-5-carboxamide

HRID 455140Notes

Reaction equation

HRID 455140 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13](F)=[CH:12][N:11]3[C:17]=2[CH2:18][C:19]2[N:23]=[C:22]([C:24]([NH:26][OH:27])=[O:25])[O:21][N:20]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2N=C3C=CC=CN3C=2CC2N=C(C(OCC)=O)ON=2)=CC=1.Cl.NO>>[OH:27][NH:26][C:24]([C:22]1[O:21][N:20]=[C:19]([CH2:18][C:17]2[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[N:23]=1)=[O:25]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 44539338HCID 44539338, compoundHCID 67028744HCID 67028744, compound

Product 1

HCID 86655128N-hydroxy-3-((2-phenylimidazo[1,2-a]pyridin-3-yl)-methyl)-1,2,4-oxadiazole-5-carboxamide

Procedure

The title compound was prepared in the same fashion as that for compound 222 from ethyl 3-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1,2,4-oxadiazole-5-carboxylate and hydroxylamine hydrochloride. m/e+=370 (M+H+). 1H NMR (400 MHz, in DMSO-d6): δ 8.43-8.41 (1H, D, d, J=7.2 Hz, ArH), δ 8.31 (1H, D, s, ArH), δ 7.88-7.86 (2H, D, d, J=8.4 Hz, ArH), δ 7.65-7.62 (1H, D, d, J=9.2 Hz, ArH), δ 7.57-7.54 (1H, D, d, J=8.4 Hz, ArH), δ 7.35-7.31 (1H, D, t, J=8.0, ArH), δ 7.04-7.00 (1H, D, t, J=8.0, ArH), and δ 4.62 (2H, D, s, CH2).

Sources & evidence

ORD record
ord-2ec0d0a4d83746d0ab3255cfd83f2ee2
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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