Lawesson's reagent → HCID 86671891, compound

HRID 331166Notes

Reaction equation

HRID 331166 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([C:9]3[C:10]([F:29])=[CH:11][C:12]([F:28])=[C:13]([C@:15]4([CH3:27])[C:21]([F:23])([F:22])[C:20]([CH3:25])([CH3:24])[O:19][CH2:18][C:17](=O)[NH:16]4)[CH:14]=3)[O:8][C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([C:9]3[C:10]([F:29])=[CH:11][C:12]([F:28])=[C:13]([C@:15]4([CH3:27])[C:21]([F:23])([F:22])[C:20]([CH3:25])([CH3:24])[O:19][CH2:18][C:17](=[S:41])[NH:16]4)[CH:14]=3)[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68380286HCID 68380286, compound

Product 1

HCID 86671891HCID 86671891, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The reaction of (R)-5-[5-(6-chloro-benzooxazol-2-yl)-2,4-difluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-one (164 mg, 359 μmol) with Lawesson's reagent (145 mg, 359 μmol) in 1,4-dioxane (3.5 ml) yielded the (R)-5-[5-(6-chloro-benzooxazol-2-yl)-2,4-difluoro-phenyl]-6,6-difluoro-5,7,7-trimethyl-[1,4]oxazepan-3-thione (148 mg, 87% yield) as a white solid. MS (ISP): m/z=473.0 [M+H]+ and 475.1 [M+2+H]+.

Sources & evidence

ORD record
ord-0412ae4035104caa998042934c9d0422
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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