Potassium Carbonate → HCID 78319529, compound

HRID 2280577Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[S:11]([C:15]1[CH:16]=[C:17]([NH:21][C:22]([C:24]2[C:25](ON3C4=NC=CC=C4N=N3)=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:23])[CH:18]=[CH:19][CH:20]=1)(=[O:14])(=[O:13])[NH2:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:25]2[C:24]([C:22]([NH:21][C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([S:11](=[O:13])(=[O:14])[NH2:12])[CH:16]=3)=[O:23])=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-Fluoro-2-methoxy-phenol (6.17 μL, 0.05 mmol), N-(3-sulfamoylphenyl)-2-(triazolo[4,5-b]pyridin-3-yloxy)quinoline-3-carboxamide (25 mg, 0.05 mmol) and K2CO3 (22.46 mg, 0.16 mmol) were combined in DMF (0.5 mL) and heated at 90° C. for 1 h. The reaction was diluted with DMF (0.5 mL), filtered, and purified by reverse phase HPLC (30-99% CH3CN/5 mM aqueous HCl) to provide 2-(4-fluoro-2-methoxy-phenoxy)-N-(3-sulfamoylphenyl)quinoline-3-carboxamide (61) (7.95 mg, 30%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.86 (s, 1H), 8.73 (s, 1H), 8.40-8.35 (m, 1H), 8.07 (dd, J=7.8, 1.6 Hz, 1H), 7.88 (td, J=4.4, 2.1 Hz, 1H), 7.72 (ddd, J=8.4, 6.9, 1.5 Hz, 1H), 7.64-7.52 (m, 4H), 7.42 (s, 2H), 7.38 (dd, J=8.9, 6.0 Hz, 1H), 7.12 (dd, J=10.8, 2.9 Hz, 1H), 6.87 (td, J=8.5, 2.9 Hz, 1H), 3.70 (s, 3H), 8.76-8.68 (m, 1H) ppm. ESI-MS m/z calc. 467.09, found 468.3 (M+1)+; Retention time: 1.78 minutes (3 minutes run).

Workup

filtrationfiltered
custompurified by reverse phase HPLC (30-99% CH3CN/5 mM aqueous HCl)

Sources & evidence

ORD record: ord-f9ecd6ced20c4cc2a4313ea4efdc7a7e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139529B2

Reaction notes

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