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

HRID 570317Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

NH2OH (10 mL, 32.1 mmol) was added in one portion to a stirred suspension of N-(5-cyano-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (49) (3.6 g, 12.85 mmol) in EtOH (100 mL). The resulting suspension was heated at 70° C. for 3 hours and then the solvent was removed to yield N-(2-fluoro-5-(N′-hydroxycarbamimidoyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (50). 1H NMR (400 MHz, d6-DMSO) δ 10.21 (s, 1H), 9.70 (s, 1H), 9.45 (td, J=1.2, 7.2 Hz, 1H), 8.61 (s, 1H), 7.95 (dd, J=2.4, 7.6 Hz, 1H), 7.79 (td, J=1.2, 8.8 Hz, 1H), 7.51-7.60 (m, 2H), 7.31-7.37 (m, 1H), 7.19 (dt, J=1.2, 6.8, 1H), 5.88 (s, 2H). MS m/z 314.1 (M+1)+.

Workup

customthe solvent was removed

Sources & evidence

ORD record: ord-826d0140ec644df28e73f67475875127
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023839B2

Reaction notes

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