Lawesson's reagent → HCID 57991970, compound

HRID 2075404Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][NH:14][C:15](=O)[CH2:16][CH2:17][C@@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)=O)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:48])=CC=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[S:48][C:15]([CH2:16][CH2:17][C@@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:19][C:20]3[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl ((1R)-4-(2-((3-fluoro-4-nitrophenyl)carbonyl)hydrazino)-4-oxo-1-((6-(trifluoromethyl)-3-pyridinyl)methyl)butyl)carbamate (214 mg, 394 μmol) and Lawesson's reagent (207 mg, 512 μmol) in THF (3 mL) was heated in a Biotage® microwave reactor at 100° C. for 15 minutes. The mixture was concentrated under reduced pressure, and the resulting yellow solid was taken up in MeOH/DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 2% to 6% MeOH/DCM) to provide tert-butyl (R)-4-(5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (190 mg, 89.1% yield) as a light yellow solid. LCMS (API-ES) m/z: 564.0 (M+Na+)

Workup

concentrationThe mixture was concentrated under reduced pressure
customabsorbed onto silica gel
custompurified by flash chromatography (silica gel, 2% to 6% MeOH/DCM)

Sources & evidence

ORD record: ord-76b77c699d3440df867d223f83f35dbd
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919504B2

Reaction notes

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