Lawesson's reagent → (R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-thione

HRID 331153Notes

Reaction equation

HRID 331153 reaction equation
[F:1][C:2]1([F:28])[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]#[C:20][C:21]2[N:22]=[C:23]([CH3:26])[S:24][CH:25]=2)[CH:16]=[CH:15][C:14]=1[F:27])[CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>O1CCOCC1>[F:1][C:2]1([F:28])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5](=[S:38])[NH:4][C@@:3]1([C:13]1[CH:18]=[C:17]([C:19]#[C:20][C:21]2[N:22]=[C:23]([CH3:26])[S:24][CH:25]=2)[CH:16]=[CH:15][C:14]=1[F:27])[CH3:12]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68379907(R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one

Product 1

HCID 86671887(R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-thioneYield 94.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-one (178 mg, 436 μmol) with Lawesson's reagent (182 mg, 436 μmol) in 1,4-dioxane (8 ml) yielded the (R)-6,6-difluoro-5-[2-fluoro-5-(2-methyl-thiazol-4-ylethynyl)-phenyl]-5,7,7-trimethyl-[1,4]oxazepan-3-thione (175 mg, 94% yield) as a light yellow foam. MS (ISP): m/z=425.1 [M+H]+ and 427.1 [M+2+H]+.

Sources & evidence

ORD record
ord-a36286d742d64a9b82911facf79bd60f
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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