3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde → 3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde O-(2-hydroxyethyl)oxime

HRID 985518Notes

Reaction equation

HRID 985518 reaction equation
Cl.[OH:2][CH2:3][CH2:4][O:5][NH2:6].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]([C:19]3[N:23]4[CH:24]=[CH:25][C:26]([CH:28]=O)=[CH:27][C:22]4=[N:21][CH:20]=3)[CH:16]=[CH:17][CH:18]=2)[CH:8]=1>>[OH:2][CH2:3][CH2:4][O:5][N:6]=[CH:28][C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([C:9]4[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=4)[CH:14]=3)=[CH:20][N:21]=[C:22]2[CH:27]=1

Participants

3

Reactant 2

HCID 99441283-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehydeHCID 22507086Ethanol, 2-(aminooxy)-, hydrochloride

Product 1

HCID 1317248043-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde O-(2-hydroxyethyl)oxime

Procedure

The title compound was prepared in a similar manner to that described in Example 14 using O-(2-hydroxyethyl)hydroxylamine hydrochloride and 3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde to afford a white crystalline solid, essentially as a single geometric isomer, m.p. 149-151° C. 1H NMR (400 MHz, CDCl3) δH 2.20 (1H, br s), 3.93-3.97 (2H, m), 4.32-4.36 (2H, m), 7.28 (1H, dd, J 2 and 7), 7.37-7.44 (1H, m), 7.58-7.68 (4H, m), 7.75 (1H, s), 7.80 (1H, s), 7.90-7.95 (1H, m), 8.17 (1H, s), 8.31 (1H, d, J 7), 8.63-8.67 (1H, m), 8.90 (1H, s); m/z (ES+) 359 (M++H).

Workup

  1. customto afford a white crystalline solid

Sources & evidence

ORD record
ord-3162a6b6f6dd4a69b978e0cf6ed624f1
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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