Tetrahydrofuran → HCID 117737078, compound

HRID 1504428Notes

Reaction equation

HRID 1504428 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([S:23](OC4C(F)=C(F)C(F)=C(F)C=4F)(=[O:25])=[O:24])=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]2=[O:38])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[NH2:39][C:40]1[CH:44]=[CH:43][O:42][N:41]=1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>Cl.CCOC(C)=O>[O:42]1[CH:43]=[CH:44][C:40]([NH:39][S:23]([C:19]2[CH:18]=[C:17]3[C:22](=[CH:21][CH:20]=2)[N:13]([C:4]2[C:3]([O:2][CH3:1])=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=2)[C:14](=[O:38])[CH:15]=[CH:16]3)(=[O:24])=[O:25])=[N:41]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 18102163-IsoxazolamineHCID 2733832Lithium HexamethyldisilazideHCID 117737072HCID 117737072, compound

Product 1

HCID 117737078HCID 117737078, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of perfluorophenyl 1-(3-methoxynaphthalen-2-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (0.250 g, 0.457 mmol), 3-aminoisoxazole (0.037 ml, 0.502 mmol) and THF (4.57 ml) was cooled in an ice-bath for 15 min, then lithium bis(trimethylsilyl)amide (1M in THF) (0.959 ml, 0.959 mmol) was added dropwise. After 60 min, the mixture was diluted with 1N aq. HCl and EtOAc. The aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was concentrated and then triturated with in Et2O. The resulting suspension was sonicated, then filtered. The collected solid was washed with Et2O (2×), dried under a stream of N2 (g), then dried under vacuum to give N-(isoxazol-3-yl)-1-(3-methoxynaphthalen-2-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.175 g, 0.391 mmol, 86% yield) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.49-11.79 (m, 1H), 8.68-8.78 (m, 1H), 8.38-8.42 (m, 1H), 8.24-8.29 (m, 1H), 7.96-8.01 (m, 2H), 7.86-7.91 (m, 1H), 7.78-7.84 (m, 1H), 7.66 (s, 1H), 7.56-7.64 (m, 1H), 7.42-7.50 (m, 1H), 6.75-6.86 (m, 2H), 6.42-6.47 (m, 1H), 3.72-3.81 (m, 3H). m/z (ESI) 447.9 (M+H)+.

Workup

  1. extractionThe aq. layer was extracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationThe residue was concentrated
  6. customtriturated with in Et2O
  7. customThe resulting suspension was sonicated
  8. filtrationfiltered
  9. washThe collected solid was washed with Et2O (2×)
  10. dry with materialdried under a stream of N2 (g)
  11. customdried under vacuum

Sources & evidence

ORD record
ord-2579f874ed044f9f9325c123c2ed75ef
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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