N,N-dimethylhydroxylamine hydrochloride → 6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide

HRID 2174242Notes

Reaction equation

HRID 2174242 reaction equation
[NH:1]([C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:19])[NH:16][CH2:17][CH3:18])[N:11]=[CH:10][C:9]=1[C:20]([OH:22])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][N:25](C)[OH:26].ON1C2C=CC=C[C:32]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH2:17]([NH:16][C:15](=[O:19])[NH:14][C:12]1[CH:13]=[C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([C:20]([N:25]([O:26][CH3:32])[CH3:24])=[O:22])=[CH:10][N:11]=1)[CH3:18]

Participants

7

Reactant 4

HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 896500056-(3-Ethylureido)-4-(phenylamino)nicotinic acid

Product 1

HCID 896503736-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-anilino-6-(ethylcarbamoylamino)pyridine-3-carboxylic acid (i) (200 mg, 0.67 mmol), dimethylhydroxylamine hydrochloride (65 mg, 0.67 mmol), 4-dimethylaminopyridine (81 mg, 0.67 mmol) and N-hydroxybenzotriazole (90 mg, 0.67 mmol) were added to a dry RBF which was flushed with N2. DMF (1.5 mL) was added and the mixture stirred. 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine hydrochloride (150 mg, 0.80 mmol) was dissolved in DMF (1.5 mL) in a separate vial and this solution added to the reaction mixture at RT. The mixture was stirred overnight at RT.

Workup

  1. customwas flushed with N2
  2. additionDMF (1.5 mL) was added
  3. additionadded to the reaction mixture at RT
  4. stirringThe mixture was stirred overnight at RT

Sources & evidence

ORD record
ord-822713183a2941bea96d1c37d5b8cf4d
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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