3-[3-(7-Formylimidazo[1,2-alpha]pyridin 3-yl)phenyl]thiophene-2-carbonitrile → 3-[3-(7-(2-Hydroxyethoxy)iminomethylimidazo[1,2-alpha]pyridin-3-yl)phenyl]thiophene-2-carbonitrile

HRID 985538Notes

Reaction equation

HRID 985538 reaction equation
Cl.[OH:2][CH2:3][CH2:4][O:5][NH2:6].[CH:7]([C:9]1[CH:14]=[CH:13][N:12]2[C:15]([C:18]3[CH:19]=[C:20]([C:24]4[CH:28]=[CH:27][S:26][C:25]=4[C:29]#[N:30])[CH:21]=[CH:22][CH:23]=3)=[CH:16][N:17]=[C:11]2[CH:10]=1)=O>>[OH:2][CH2:3][CH2:4][O:5][N:6]=[CH:7][C:9]1[CH:14]=[CH:13][N:12]2[C:15]([C:18]3[CH:19]=[C:20]([C:24]4[CH:28]=[CH:27][S:26][C:25]=4[C:29]#[N:30])[CH:21]=[CH:22][CH:23]=3)=[CH:16][N:17]=[C:11]2[CH:10]=1

Participants

3

Reactant 2

HCID 99020133-[3-(7-Formylimidazo[1,2-alpha]pyridin 3-yl)phenyl]thiophene-2-carbonitrileHCID 22507086Ethanol, 2-(aminooxy)-, hydrochloride

Product 1

HCID 853257033-[3-(7-(2-Hydroxyethoxy)iminomethylimidazo[1,2-alpha]pyridin-3-yl)phenyl]thiophene-2-carbonitrile

Procedure

The title compound was prepared in a similar manner to that described in Example 14 using O-(2-hydroxyethyl)hydroxylamine hydrochloride (93 mg, 0.82 mmol) and 3-[3-(7-formylimidazo[1,2-α]pyridin -3-yl)phenyl]thiophene-2-carbonitrile (67 mg, 0.20 mmol) to afford a white crystalline solid (43 mg, 55%), essentially as a single geometric isomer, m.p. 224-225° C. 1H NMR (360 MHz, CDCl3) δH 3.94-3.97 (2H, m), 4.32-4.36 (2H, m), 7.31-7.38 (2H, m), 7.64-7.72 (5H, m), 7.80 (1H, s), 7.88 (1H, s), 8.17 (1H, s), 8.47 (1H, d, J 7); m/z (ES+) 389 (M++H).

Sources & evidence

ORD record
ord-65dd1c5f079a4a758e7d194ffdc6cfcc
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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