Dimethylamine → 2-Amino-5-bromo-N,N-dimethylnicotinamide

HRID 241059

Reaction equation

HRID 241059 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].[CH3:12][NH:13][CH3:14].C(P(C#N)(CC)=O)C.C(N(CC)CC)C>O1CCCC1>[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([N:13]([CH3:14])[CH3:12])=[O:5]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 7374452-Amino-5-bromonicotinic acidHCID 13586794Diethylphosphorylcyanide

Product 1

HCID 575375472-Amino-5-bromo-N,N-dimethylnicotinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-amino-5-bromonicotinic acid (0.35 g, 1.61 mmol) in tetrahydrofuran (5 mL) was added dimethylamine (0.8 mL of a 2M solution in tetrahydrofuran, 1.60 mmol), diethylphosphoryl cyanide (0.29 g, 1.77 mmol), and triethylamine (0.34 g, 3.38 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min and then at room temperature for 4 h. Concentration and purification by column chromatography on silica (5-10% methanol in dichloromethane) gave the title Compound as a white solid. MS (EI) for C8H10BrN3O: 244 (MH+).

Workup

  1. waitat room temperature for 4 h
  2. concentrationConcentration and purification by column chromatography on silica (5-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7eb2afd095d64758978e9225e02497c7
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Linked notes

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