Lawesson's reagent → HCID 86671879, compound

HRID 331142Notes

Reaction equation

HRID 331142 reaction equation
[F:1][C:2]1([F:32])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=O)[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:23]=2)[CH:16]=[CH:15][C:14]=1[F:31])[CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>O1CCOCC1>[F:1][C:2]1([F:32])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[S:42])[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([C:19]2[CH:20]=[N:21][N:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:23]=2)[CH:16]=[CH:15][C:14]=1[F:31])[CH3:12]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380281HCID 68380281, compound

Product 1

HCID 86671879HCID 86671879, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-6,6-difluoro-5-{2-fluoro-5-[1-(4-fluoro-phenyl)-1H-pyrazol-4-yl]-phenyl}-5,7,7-trimethyl-[1,4]oxazepan-3-one (189 mg, 422 μmol) with Lawesson's reagent (139 mg, 338 μmol) in 1,4-dioxane (14 ml) yielded the (R)-6,6-difluoro-5-{2-fluoro-5-[1-(4-fluoro-phenyl)-1H-pyrazol-4-yl]-phenyl}-5,7,7-trimethyl-[1,4]oxazepan-3-thione (148 mg, 76% yield) as a white solid. MS (ISP): m/z=464.2.0 [M+H]+.

Sources & evidence

ORD record
ord-388cb13fb9d34448a9893cd50717d65b
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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