1,2-Dichloroethane → 4-Amino-N-methylpyridine-3-carboxamide

HRID 1887702Notes

Reaction equation

HRID 1887702 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:24][C:22]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]([NH:24][CH3:22])=[O:10])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3199794-Aminonicotinic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 588352554-Amino-N-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 4-aminonicotinic acid (691 mg, 5.0 mmol), methylamine hydrogen chloride (410 mg, 1.2 eq), EDC (1.15 g, 1.2 eq), HOBt (810 mg, 1.2 eq) in DMF (20 mL) was added DIEA (3.0 mL, 3.0 eq). The mixture was stirred at room temperature overnight. It was concentrated and dissolved in EtOAc. It was washed with saturated NaHCO3 solution. It was concentrated and purified by silica gel with chromatography (0%˜20% MeOH/DCM) to obtain the desired product 4-amino-N-methylnicotinamide.

Workup

  1. concentrationIt was concentrated
  2. dissolutiondissolved in EtOAc
  3. washIt was washed with saturated NaHCO3 solution
  4. concentrationIt was concentrated
  5. custompurified by silica gel with chromatography (0%˜20% MeOH/DCM)

Sources & evidence

ORD record
ord-eddce89a73b345a6a420f7694bcb8717
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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