Ammonia → AZD7118 Bromo Amide

HRID 1047140Notes

Reaction equation

HRID 1047140 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%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-bromo-2-(3-ethylureido)isonicotinate (Intermediate 4, 261 g, 865 mmol) and 7N ammonia in methanol (1.7 L) was allowed to stir at room temperature for 3 d. The solid that precipitated was then collected by filtration, rinsed with methanol (2×500 mL), and then dried on a high vacuum pump overnight, yielding 237 g (95%) of 5-bromo-2-(3-ethylureido)isonicotinamide as a smooth white solid.

Workup

  1. customThe solid that precipitated
  2. filtrationwas then collected by filtration
  3. washrinsed with methanol (2×500 mL)
  4. customdried on a high vacuum pump overnight

Sources & evidence

ORD record
ord-5f9830b40179458fbc8f695e4589c15f
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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