Lawesson's reagent → HCID 86671877, compound

HRID 331138Notes

Reaction equation

HRID 331138 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([F:27])=[C:12]([C@:14]3([CH3:26])[C:20]([F:22])([F:21])[C:19]([CH3:24])([CH3:23])[O:18][CH2:17][C:16](=O)[NH:15]3)[CH:13]=2)[CH:5]=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([F:27])=[C:12]([C@:14]3([CH3:26])[C:20]([F:22])([F:21])[C:19]([CH3:24])([CH3:23])[O:18][CH2:17][C:16](=[S:37])[NH:15]3)[CH:13]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380410HCID 68380410, compound

Product 1

HCID 86671877HCID 86671877, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-5-[5-(5-chloro-pyridin-3-yl)-2-fluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-one (235 mg, 589 μmol) with Lawesson's reagent (238 mg, 589 μmol) in 1,4-dioxane (19.6 ml) yielded the (R)-5-[5-(5-chloro-pyridin-3-yl)-2-fluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (211 mg, 86% yield) as a white solid. MS (ISP): m/z=415.1 [M+H]+ and 417.1 [M+2+H]+.

Sources & evidence

ORD record
ord-18e328f065a645c99c9171cc162c5f82
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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