HCID 19365026, compound → HCID 59526799, compound

HRID 1920698Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([O:21]CC)=O)=[C:5]2[SH:24])[CH2:3][CH2:2]1.[CH:25]1([N:28]2C3C(=CC(F)=C(F)C=3)C(=O)C3C(O)=C(C#N)SC2=3)C[CH2:26]1>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]3[C:19]([OH:21])=[C:26]([C:25]#[N:28])[S:24][C:5]2=3)[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 19365026HCID 19365026, compound

HCID 178470122HCID 178470122, compound

Product 1

HCID 59526799HCID 59526799, compound

Procedure

The title compound is prepared from ethyl 1-cyclopropyl-6,7-difluoro-2-mercapto-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (See US 2008071086, which is hereby incorporated by reference for its teachings regarding this and other compounds, see also, Hashimoto, et al., 2007) using a procedure analogous to that describing the preparation of 9-cyclopropyl-6,7-difluoro-3-hydroxyl-4-oxo-4,9-dihydrothieno[2,3-b]quinoline-2-carbonitrile. (Chiba, et al., JP 03-223289) The crude product is purified by recrystallization from DMF to give the title compound as a white solid. 1H NMR: δ 1.04 (m, 2H), 1.27 (m, 2H), 3.90 (m, 1H), 4.02 (d, J=1.5 Hz, 3H), 7.89 (dd, J=10.0 Hz, 8.5 Hz, 1H). 19F NMR: δ −145.0 (d, J=22.5 Hz, 1F), −138.9 (d, J=22.5 Hz, 1F). LCMS (APCI): m/z calcd for C16H10F2N2O3S ([M]+) 348. found 349 ([M+H]+).

Workup

custom(Chiba, et al., JP 03-223289) The crude product is purified by recrystallization from DMF

Sources & evidence

ORD record: ord-ccbecad9087e4fc6a143a1a7e9573eed
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173636B2

Reaction notes

Loading…