Lawesson's reagent → HCID 86636677, compound

HRID 2075401Notes

Reaction equation

HRID 2075401 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:29][C:30]1[CH:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=1)[CH2:10][CH2:11][C:12]([NH:14][NH:15][C:16]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[N:23][C:22]([F:28])=[CH:21]2)=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:49])=CC=1>C1COCC1.C(Cl)Cl>[F:28][C:22]1[N:23]=[CH:24][C:25]2[C:20]([CH:21]=1)=[CH:19][C:18]([C:16]1[S:49][C:12]([CH2:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:29][C:30]3[CH:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=3)=[N:14][N:15]=1)=[CH:27][CH:26]=2

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 67089308HCID 67089308, compound

Product 1

HCID 86636677HCID 86636677, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)—N′-(4-(tert-butyloxycarbonylamino)-5-(6-(trifluoromethyl)pyridin-3-yl)pentanoyl)-3-fluoroisoquinoline-6-carbohydrazide (108 mg, 207 μmol) and Lawesson's reagent (101 mg, 249 μmol) in THF (2 mL) was heated in a Biotage® microwave reactor at 100° C. for 10 minutes. The mixture was diluted with DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 2-8% MeOH/DCM) providing tert-butyl (R)-4-(5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (96 mg, 88%) as a white solid. LCMS (API-ES) m/z: 548.1 (M+H+).

Workup

  1. customabsorbed onto silica gel
  2. custompurified by flash chromatography (silica gel, 2-8% MeOH/DCM)

Sources & evidence

ORD record
ord-4fc58c8ecbb34679ba98a4964eb2bf01
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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