Ammonia → 5-(2-Acetamido-5-methylpyridin-4-yl)-2-bromo-3-furamide

HRID 537064Notes

Reaction equation

HRID 537064 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([Br:16])=[C:13]([C:17](O)=[O:18])[CH:12]=2)[C:8]([CH3:20])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C(Cl)(=O)OCC(C)C.[NH3:29]>C1COCC1>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([Br:16])=[C:13]([C:17]([NH2:29])=[O:18])[CH:12]=2)[C:8]([CH3:20])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 667484985-(2-Acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoic acid

Product 1

HCID 667482995-(2-Acetamido-5-methylpyridin-4-yl)-2-bromo-3-furamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoic acid (10.0 g, 29.6 mmol) in THF (950 mL) at −20° C. was added TEA (4.55 mL, 32.5 mmol) over 20 min. The reaction mixture was allowed to stir for 10 min after addition was complete and then isobutyl carbonochloridate (10.7 g, 88.8 mmol) was added over 10 min. The reaction mixture was allowed to stir for 20 min at −20° C. and was then allowed to warm to rt. A solution of NH3 in THF was added and the reaction mixture was allowed to stir at rt overnight. The mixture was concentrated and the residue was diluted with water and filtered to give 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furamide (8.5 g, 85%).

Workup

  1. additionafter addition
  2. stirringto stir for 20 min at −20° C.
  3. stirringto stir at rt overnight
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-aba29e138e124c95957805a9af90cb37
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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