1-Hydroxybenzotriazole → 2-amino-5-bromo-N-methoxy-N-methylnicotinamide

HRID 2387215Notes

Reaction equation

HRID 2387215 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:44][O:45][NH:46][CH3:47]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([N:46]([O:45][CH3:44])[CH3:47])=[O:5]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 7374452-Amino-5-bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 596997242-amino-5-bromo-N-methoxy-N-methylnicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Amino-5-bromonicotinic acid (1 g, 4.6 mmol) in DMF (15 ml) is added EDC hydrochloride (1.06 g, 5.53 mmol), HOBt (0.747 g, 5.53 mmol), diisopropylethylamine (2 ml, 11.5 mmol) and N-methoxy-N-methylamine hydrochloride (0.54 g, 5.53 mmol), and the resulting solution is stirred at room temperature overnight. The reaction is concentrated in vacuo, and the residue is dissolved in EtOAc, washed with sat. aq. NaHCO3, dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (SiO2, 0-10% ethanol in DCM) yields 2-Amino-5-bromo-N-methoxy-N-methyl-nicotinamide.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (SiO2, 0-10% ethanol in DCM)

Sources & evidence

ORD record
ord-49a8fb6aa17f4cd4bc6b2a8a58a6dcaf
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Reaction notes

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