Triethylamine → 5-bromo-N-cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxamide

HRID 58046Notes

Reaction equation

HRID 58046 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([OH:11])=O)[CH:3]=1.CCN(CC)CC.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>CN(C=O)C>[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([NH:22][CH:19]2[CH2:21][CH2:20]2)=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 27643145-Bromo-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 897817445-bromo-N-cyclopropyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylic acid (200 mg, 0.917 mmol), Et3N (0.1 mL), and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (348 mg, 0.917 mmol) in DMF (5 mL) was added cyclopropanamine (52.4 mg, 0.917 mmol). The mixture was stirred at room temperature for 2 hours and purified via preparative HPLC, eluting with a gradient of 1-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The product was dried under vacuum to give the title compound.

Workup

  1. custompurified via preparative HPLC
  2. washeluting with a gradient of 1-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)
  3. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-baeb0c1f09fa4fdeb69bc83c98cd7852
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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