Lawesson's reagent → HCID 86671889, compound

HRID 331164Notes

Reaction equation

HRID 331164 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[C:11]([F:30])=[CH:12][C:13]([F:29])=[C:14]([C@:16]3([CH3:28])[C:22]([F:24])([F:23])[C:21]([CH3:26])([CH3:25])[O:20][CH2:19][C:18](=O)[NH:17]3)[CH:15]=2)[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[C:11]([F:30])=[CH:12][C:13]([F:29])=[C:14]([C@:16]3([CH3:28])[C:22]([F:24])([F:23])[C:21]([CH3:26])([CH3:25])[O:20][CH2:19][C:18](=[S:40])[NH:17]3)[CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380421HCID 68380421, compound

Product 1

HCID 86671889HCID 86671889, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-5-[5-(3-chloro-phenylethynyl)-2,4-difluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-one (622 mg, 1.14 mmol) with Lawesson's reagent (572 mg, 1.41 mmol) in 1,4-dioxane (40 ml) yielded the (R)-5-[5-(3-chloro-phenylethynyl)-2,4-difluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (432 mg, 67% yield) as a light brown gum.

Sources & evidence

ORD record
ord-c5ae3813b2ae4e5ab8c15d4a7ad31c5e
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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