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-dimethylaminoethyl)oxime

HRID 985519Notes

Reaction equation

HRID 985519 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][O:6][NH2:7].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:16]=[C:17]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([CH:30]=O)=[CH:29][C:24]4=[N:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:10]=1>>[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][O:6][N:7]=[CH:30][C:28]1[CH:27]=[CH:26][N:25]2[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:11]4[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=4)[CH:16]=3)=[CH:22][N:23]=[C:24]2[CH:29]=1

Participants

3

Reactant 2

HCID 99441283-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehydeHCID 21928691Dimethylaminoethoxyamine hydrochloride

Product 1

HCID 1317248053-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehyde O-(2-dimethylaminoethyl)oxime

Procedure

The title compound was prepared in a similar manner to that described in Example 14 using O-(2-dimethylaminoethyl)hydroxylamine hydrochloride and 3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde to afford a brown oil, essentially as a single geometric isomer. 1H NMR (400 MHz, CDCl3) δH 2.97 (6H, s), 3.43-3.47 (2H, m), 4.65-4.69 (2H, m), 7.28-7.33 (2H, m), 7.42-7.47 (1H, m), 7.62-7.82 (4H, m), 7.94-7.98 (1H, m), 8.20 (1H, s), 8.32-8.35 (1H, m), 8.25 (1H, s), 8.61-8.65(1H, m), 8.90 (1H, s); m/z (ES+) 386 (M++H).

Workup

  1. customto afford a brown oil

Sources & evidence

ORD record
ord-25983a5ea2bc4eb69659bc675b6207b9
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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