Thionyl Chloride → HCID 86730090, compound

HRID 880036Notes

Reaction equation

[CH2:1]([O:5][C:6]1[C:7](=[O:21])[N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:9]=[CH:10][C:11]=1[C:12](OCC)=[O:13])[CH:2]([CH3:4])[CH3:3].S(Cl)([Cl:24])=O>>[CH2:1]([O:5][C:6]1[C:7](=[O:21])[N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:9]=[CH:10][C:11]=1[C:12]([Cl:24])=[O:13])[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 86730091HCID 86730091, compound2×

Product 1

HCID 86730090HCID 86730090, compoundYield 93%

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 3-isobutoxy-1-isobutyl-2-oxo-1,2-dihydropyridine-4-carboxylate (Intermediate 8) (100 mg, 0.339 mmol) was added thionyl chloride (24.71 μL, 0.3390 mmol). The reaction mixture was stirred at 80° C. for 3 h. The solvent was evaporated under reduced pressure to give Example 52A which was used without further purification (90 mg, 0.315 mmol, 93% yield). LCMS RT=1.89 min [M+MeO+1]=282 {(MeOH/H2O/TFA) Phenom. Luna C18; 50×4.6 mm; 4 min Grad}.

Workup

customThe solvent was evaporated under reduced pressure
customto give Example 52A which
customwas used without further purification (90 mg, 0.315 mmol, 93% yield)
custom4 min Grad}

Sources & evidence

ORD record: ord-bcf0d0346c1f4664b5efc90e450cf752
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993557B2

Reaction notes

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