Triethylamine → HCID 67086709, compound

HRID 1665160Notes

Reaction equation

HRID 1665160 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[CH:20]([N:23]=[C:24]=[O:25])([CH3:22])[CH3:21]>CN(C=O)C.CCOC(C)=O>[CH2:8]([O:7][C:5](=[O:6])[C:4]1[CH:10]=[CH:11][N:12]=[C:2]([NH:1][C:24]([NH:23][CH:20]([CH3:22])[CH3:21])=[O:25])[CH:3]=1)[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 7015521Ethyl 2-aminopyridine-4-carboxylate

Product 1

HCID 67086709HCID 67086709, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of ethyl 2-aminoisonicotinate (500 mg, 3.01 mmol) in DMF (10 ml) is added triethylamine (1.26 ml, 9.03 mmol) and then isopropyl isocyanate (512 mg, 6.02 mmol). The reaction mixture is heated in a microwave at 140° C. for 2 hours. The reaction mixture is diluted with EtOAc, washed with water (×5), brine, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, MeOH/DCM) affords 2-(3-Isopropyl-ureido)-isonicotinic acid ethyl ester; [M+H]+ 252

Workup

  1. washwashed with water (×5), brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16e7ce30f8f7410c8949638e378f22b6
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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