Lawesson's reagent → AZD7118 Bromo Thioamide

HRID 1047141Notes

Reaction equation

HRID 1047141 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>O1CCCC1>[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 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A suspended mixture of 5-bromo-2-(3-ethylureido)isonicotinamide (Intermediate 5, 237 g, 830 mmol), Lawesson's Reagent (336 g, 830 mmol), and tetrahydrofuran (3 L) was stirred at 70° C. for 18 h. The precipitate was collected by filtration and washed with methyl tert-butyl ether (2×500 L). This solid was then dried in the vacuum oven at 50° C. for 12 h to give 192 g (77%) of 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide as an off white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with methyl tert-butyl ether (2×500 L)
  3. customThis solid was then dried in the vacuum oven at 50° C. for 12 h

Sources & evidence

ORD record
ord-2f6881b60487450b9c0111a99f6f0781
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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