Ammonia → AZD7118 Bromo Amide

HRID 2061844Notes

Reaction equation

HRID 2061844 reaction equation
[Br:1][C:2]1[C:7]([C:8](OC)=[O:9])=[CH:6][C:5]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])=[N:4][CH:3]=1.[NH3:18]>CO>[Br:1][C:2]1[C:7]([C:8]([NH2:18])=[O:9])=[CH:6][C:5]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59416007Methyl 5-bromo-2-(3-ethylureido)isonicotinate2×

Product 1

HCID 59208425AZD7118 Bromo AmideYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-bromo-2-(3-ethylureido)isonicotinate (Intermediate 1, 56.22 g, 186.0 mmol) in 7N ammonia in methanol (1 L) was allowed to stir at room temperature in a sealed flask for 1½ d. The precipitate that formed was collected by filtration, rinsed with acetonitrile (500 mL), and then dried on the high vacuum pump overnight, yielding 50.8 g of a solid (95.1%).

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washrinsed with acetonitrile (500 mL)
  4. customdried on the high vacuum pump overnight

Sources & evidence

ORD record
ord-332ea4bf248e4bceb9b805eb835e8b83
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

Loading…