Hydroxyamine hydrochloride → 3'-(7-Hydroxyiminomethylimidazo [1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrile

HRID 985543Notes

Reaction equation

HRID 985543 reaction equation
Cl.[NH2:2][OH:3].[CH:4]([C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:16]=[C:17]([C:21]4[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:18]=[CH:19][CH:20]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1)=O>>[OH:3][N:2]=[CH:4][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:16]=[C:17]([C:21]4[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:18]=[CH:19][CH:20]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 98583783'-(7-Formylimidazo[1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrile

Product 1

HCID 1364734673'-(7-Hydroxyiminomethylimidazo [1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrile

Procedure

The title compound was prepared in a similar manner to that described in Example 14 using hydroxylamine hydrochloride (77 mg, 1.11 mmol) and 3′-(7-formylimidazo[1,2-α]pyridin-3-yl)biphenyl-2-carbonitrile (120 mg, 0.37 mmol) to afford a white crystalline solid (105 mg, 83%), essentially as a single geometric isomer. 1H NMR (400 MHz, d6-DMSO) δH 7.27 (1H, dd, J 1 and 7), 7.61-7.90 (8H, m), 7.90 (2H, s), 8.00 (1H, dd, J 8 and 1), 8.25 (1H, s), 8.68 (1H, d, J 7), 11.53 (1H, s); m/z (ES+) 339 (M++H).

Sources & evidence

ORD record
ord-908f52ebd1454fab8feffeecccbebb7b
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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