2-Aminopyridine → HCID 57690166, compound

HRID 2178545Notes

Reaction equation

HRID 2178545 reaction equation
Br[CH:2]([CH3:10])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>COCCOC>[CH3:10][C:2]1[N:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]2=[N:11][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 11117285Ethyl 3-bromo-2-oxobutanoate

Product 1

HCID 57690166HCID 57690166, compoundYield 115.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of compound 1-B (1.25 g, 5.98 mmol) in DME (5 mL) was added 2-aminopyridine (0.563 g, 5.98 mmol) and the reaction mixture was allowed to warm to room temperature and stir for 18 h. The precipitate was filtered, washed with DME and dried in vacuo to afford 1.41 g of a white solid. The solid was dissolved in MeOH (20 mL) and refluxed for 18 h. The reaction mixture was cooled and the solvent evaporated under reduced pressure. The crude residue was partitioned between EtOAc and 10% NaHCO3, the layers separated and the organic phase washed with 10% NaHCO3, H2O, brine, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure to afford 0.902 g of a white solid. The crude solid was purified by flash column chromatography (SiO2) eluting with a heptanes-EtOAc gradient to afford compound 1-C as a white solid (0.842 g, 69%). 1H-NMR (CDCl3): δ 7.90-7.92 (d, 1H), 7.65-7.68 (d, 1H), 7.21-7.25 (q, 1H), 6.88-6.92 (t, 1H), 4.44-4.50 (q, 2H), 2.80 (s, 3H), 1.44-1.48 (t, 3H); MS: m/z 205.2 (MH+).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with DME
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ef5e30e5b4564754982513535f20f580
Source dataset
uspto-grants-2015_06
Patent number
US09067935B2

Reaction notes

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