Hydroxylamine → 6-fluoro-N-[5-[(Z)-N'-hydroxycarbamimidoyl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide

HRID 405792Notes

Reaction equation

HRID 405792 reaction equation
[NH2:1][OH:2].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:24])=[C:9]([NH:11][C:12]([C:14]2[N:18]3[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[CH:10]=1)#[N:4]>>[F:23][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C:12]([NH:11][C:9]3[CH:10]=[C:5](/[C:3](=[N:1]/[OH:2])/[NH2:4])[CH:6]=[CH:7][C:8]=3[CH3:24])=[O:13])=[CH:15][N:16]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 71280520N-(5-cyano-2-methylphenyl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 894212156-fluoro-N-[5-[(Z)-N'-hydroxycarbamimidoyl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide

Conditions

Temperature
60 °C

Procedure

NH2OH (5 mL, 16.1 mmol) was added in one portion to a stirred suspension of N-(5-cyano-2-methylphenyl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide (39) (0.95 g, 3.23 mmol). The resulting suspension was heated at 60° C. overnight and then cooled to 0° C. The product, (Z)-6-fluoro-N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (40) was collected by filtration. MS m/z 328.1 (M+1)+.

Workup

  1. temperaturecooled to 0° C
  2. filtrationThe product, (Z)-6-fluoro-N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (40) was collected by filtration

Sources & evidence

ORD record
ord-875d3ad7ea944e79a3817657d94d3582
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

Loading…