Lawesson's reagent → HCID 86671890, compound

HRID 331165Notes

Reaction equation

HRID 331165 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=2)=[CH:4][C:3]=1[C@:17]1([CH3:29])[C:23]([F:25])([F:24])[C:22]([CH3:27])([CH3:26])[O:21][CH2:20][C:19](=O)[NH:18]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=2)=[CH:4][C:3]=1[C@:17]1([CH3:29])[C:23]([F:25])([F:24])[C:22]([CH3:27])([CH3:26])[O:21][CH2:20][C:19](=[S:39])[NH:18]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380082HCID 68380082, compound

Product 1

HCID 86671890HCID 86671890, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-5-[2,4-difluoro-5-(2-methoxy-pyrimidin-5-yl)-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-one (82 mg, 198 μmol) with Lawesson's reagent (80.2 mg, 198 μmol) in 1,4-dioxane (3 ml) yielded the (R)-5-[2,4-difluoro-5-(2-methoxy-pyrimidin-5-yl)-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (53 mg, 62% yield) as a white solid. MS (ISP): m/z=430.3 [M+H]+.

Sources & evidence

ORD record
ord-b570308dab0d4ff9a304cbdbbb497b0b
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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