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

HRID 2288321Notes

Reaction equation

HRID 2288321 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.CN(C)C=O.C(OCC)(=O)C>[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

7

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 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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-methylamino-nicotinate in 25 ml of dimethylformamide 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 sulphate 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 the crude product
  3. customobtained
  4. washthe organic phase was washed with water
  5. dry with materialafter drying over sodium sulphate it
  6. customThe residue obtained
  7. customwas purified by flash chromatography (silica gel; gradient: dichloromethane to dichloromethane/ethanol=19:1)

Sources & evidence

ORD record
ord-92c9897b334a458ea7001babe9ecab4e
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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