Ethanol → 1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic Acid [4-(6-aminofuro[3,2-c]pyridin-7-yloxymethyl)phenyl]amide

HRID 912052Notes

Reaction equation

[N+:1]([C:4]1[N:9]=[CH:8][C:7]2[CH:10]=[CH:11][O:12][C:6]=2[C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[C:25](=[O:37])[N:26]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)=[O:23])=[CH:17][CH:16]=1)([O-])=O.CCO.[NH4+].[Cl-]>[Fe].ClCCCl>[NH2:1][C:4]1[N:9]=[CH:8][C:7]2[CH:10]=[CH:11][O:12][C:6]=2[C:5]=1[O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]2[C:25](=[O:37])[N:26]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[CH:27]=[CH:28][CH:29]=2)=[O:23])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 75 °C

Procedure

The mixture of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid [4-(6-nitrofuro[3,2-c]pyridin-7-yloxymethyl)phenyl]amide (13.8 mg, 0.0248 mmol), iron powder (62 mg, 1.1 mmol), EtOH (1.5 ml), 1,2-Dichloroethane (1.5 ml), and saturated NH4Cl (0.3 ml) was heated at 75° C. for 30 min. After that time, the solvent was removed, and it was then dissolved in DMSO for Gilson HPLC purification. It gave the title compound as a light-yellow solid. 1H NMR (400 MHz, CDCl3): δ=4.55 (brs, 2H), 5.35 (s, 2H), 6.60 (dd, J=6.8 & 7.2 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 7.24-7.29 (m, 2H), 7.38-7.43 (m, 4H), 7.43 (d, J=2.4 Hz, 1H), 7.60 (dd, J=2.0 & 6.8 Hz, 1H), 7.73 (dd, J=2.0 & 6.4 Hz, 2H), 8.07 (s, 1H), 8.75 (dd, J=2.0 & 6.8 Hz, 1H), 11.85 (brs, 1H). MS (ES+): m/z 471.05 [MH+]. HPLC: tR=2.60 min (polar—5 min, ZQ3).

Workup

customAfter that time, the solvent was removed
dissolutionit was then dissolved in DMSO for Gilson HPLC purification

Sources & evidence

ORD record: ord-9f6a5d61ce434bd9adff92cffec23f8a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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