Ammonia → 5-Bromo-2-(3-propylureido)isonicotinamide

HRID 2061858Notes

Reaction equation

HRID 2061858 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][CH2:17][CH3:18])=[O:14])=[N:4][CH:3]=1.[NH3:19]>CO>[Br:1][C:2]1[C:7]([C:8]([NH2:19])=[O:9])=[CH:6][C:5]([NH:12][C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59415825Methyl 5-bromo-2-(3-propylureido)isonicotinate2×

Product 1

HCID 594161565-Bromo-2-(3-propylureido)isonicotinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-bromo-2-(3-propylureido)isonicotinate (Intermediate 42, 128 g, 405 mmol) and 7N ammonia in methanol (1 L) was allowed to stir at room temperature for 3 d. Stirring for the reaction was then stopped and the solids were allowed to settle. The precipitated was then vacuum filtered, rinsed with methanol (2×500 mL), and then dried on the high vacuum pump overnight, yielding 123 g (quant) of 5-bromo-2-(3-propylureido)isonicotinamide as a white solid.

Workup

  1. stirringStirring for the reaction
  2. filtrationvacuum filtered
  3. washrinsed with methanol (2×500 mL)
  4. customdried on the high vacuum pump overnight

Sources & evidence

ORD record
ord-dd404ab99a1f4cc1b3f1850486d2f248
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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