Lawesson's reagent → AZD7118 Bromo Thioamide

HRID 2243063Notes

Reaction equation

HRID 2243063 reaction equation
[Br:1][C:2]1[C:7]([C:8]([NH2:10])=O)=[CH:6][C:5]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1COCC1>[Br:1][C:2]1[C:7]([C:8](=[S:26])[NH2:10])=[CH:6][C:5]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59208425AZD7118 Bromo Amide2×

Product 1

HCID 59208439AZD7118 Bromo ThioamideYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-bromo-2-(3-ethylureido)isonicotinamide (Intermediate 43, 1.25 g, 4.35 mmol) in THF (20 mL), was added Lawessons reagent (1.761 g, 4.35 mmol). The reaction mixture was then heated to 70° C. overnight. The solid that formed was collected by filtration and washed with THF to provide 1 g of desired product. MS (ESP): 304 (M+1) for C19H11BrN4OS

Workup

  1. customThe solid that formed
  2. filtrationwas collected by filtration
  3. washwashed with THF

Sources & evidence

ORD record
ord-cdab20468e454cfcb0cb42464e58b152
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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