Hydrochloric Acid → HCID 117739242, compound

HRID 708798Notes

Reaction equation

HRID 708798 reaction equation
[F:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[C:5](=[O:15])[NH:4][CH:3]1OC.Cl.O1CCOCC1>C(#N)C>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[C:5](=[O:15])[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 117740417HCID 117740417, compound

Product 1

HCID 117739242HCID 117739242, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of Intermediate 3D (8.1 g, 33.7 mmol) in acetonitrile (100 mL) was added 4.0N HCl in dioxane (25.3 mL, 101 mmol). The mixture was stirred at 65° C. for 1.5 h. HPLC and LCMS indicated complete conversion of starting material. Solvent was removed to give Intermediate 3E (8.1 g, 33.1 mmol, 98% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.38-8.46 (m, 2H) 8.31 (dd, J=8.79, 2.20 Hz, 1H) 7.61 (d, 1H); 19F NMR (376 MHz, DMSO-d6) δ ppm −160.17 (s., 1F); MS (ESI) m/z: 209.2 (M+H)+.

Workup

  1. customSolvent was removed

Sources & evidence

ORD record
ord-83c2b1d7d4e548e1b092e4555d44f4cc
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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