Imidazolate → Methyl 5-[2-(4-cyanophenyl)ethylcarbonylamino]-6-methylamino-nicotinate

HRID 50191

Reaction equation

HRID 50191 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[N-]1C=CN=C1.[NH2:19][C:20]1[C:21]([NH:30][CH3:31])=[N:22][CH:23]=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([NH:19][C:20]2[C:21]([NH:30][CH3:31])=[N:22][CH:23]=[C:24]([CH:29]=2)[C:25]([O:27][CH3:28])=[O:26])=[O:13])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 3386966ImidazolateHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 18412673Methyl 5-amino-6-(methylamino)pyridine-3-carboxylate

Product 1

HCID 18412623Methyl 5-[2-(4-cyanophenyl)ethylcarbonylamino]-6-methylamino-nicotinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.6 g (15 mmol) of 3-(4-cyanophenyl)propionic acid in 25 mL of absolute tetrahydrofuran was mixed with 2.4 g (15 mmol) of N,N′-carbonyldiimidazole and stirred for 20 minutes at room temperature. Then the imidazolide was mixed with a solution of 2.3 g (13 mmol) of methyl 5-amino-6-methylaminonicotinate in 25 mL of dimethyfformamide and heated for 3 hours to 100° C. After the removal of the solvent in vacuo, the crude product obtained was taken up in ethyl acetate, the organic phase was washed with water and after drying over sodium sulfate it was again freed from solvent. The residue obtained was purified by flash chromatography (silica gel; gradient: dichloromethane to dichloromethane/ethanol=19:1). Yield: 2.1 g (50% of theory) of beige solid; Rf value: 0.54 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

Workup

  1. temperatureheated for 3 hours to 100° C
  2. customAfter the removal of the solvent in vacuo

Sources & evidence

ORD record
ord-8ed547a2fc2a4ce58ab475f72df20328
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Linked notes

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