Propionic Acid → N-(5-bromopyridin-3-yl)propionamide

HRID 1878615Notes

Reaction equation

HRID 1878615 reaction equation
[C:1]([OH:5])(=O)[CH2:2][CH3:3].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([Br:35])[CH:34]=1.CN1CCOCC1>CN(C=O)C>[Br:35][C:33]1[CH:34]=[C:29]([NH:28][C:1](=[O:5])[CH2:2][CH3:3])[CH:30]=[N:31][CH:32]=1

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 8176813-Amino-5-bromopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68737458N-(5-bromopyridin-3-yl)propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of propionic acid (Sigma-Aldrich, St. Louis, USA) (1.5 eq, 8.4 mmol, 0.63 ml) in DMF (15 ml), HOBt (1.2 eq, 6.7 mmol, 0.910 g) and EDC hydrochloride (1.5 eq, 8.4 mmol, 1.65 g) are added. The resulting mixture is stirred for 1 h at r.t. Then 3-amino-5-bromopyridine (Sigma-Aldrich, St. Louis, USA) (1 eq, 5.6 mmol, 1.00 g) and N-methyl-morpholine (3 eq, 16.8 mmol, 1.85 ml) are added and stirring is continued for 18 h at r.t. The solvents are evaporated and the residue is purified by column chromatography (hexane/EtOAc) yielding the title compound; [M+H]+=230.

Workup

  1. stirringstirring
  2. waitis continued for 18 h at r.t
  3. customThe solvents are evaporated
  4. customthe residue is purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-6397897a2c1e47e4a2a6da01346ae3a5
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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