2,6-Lutidine → (7-Pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-carbamic acid ethyl ester

HRID 229356Notes

Reaction equation

HRID 229356 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:9][C:10]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=O.[N:18]1[C:23](C)=[CH:22][CH:21]=[CH:20][C:19]=1C>CN1CCN(C)C1=O.CCOC(C)=O>[CH2:15]([O:14][C:13](=[O:17])[NH:12][C:10]1[N:1]=[C:2]2[CH:7]=[C:6]([C:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=3)[CH:5]=[CH:4][N:3]2[CH:9]=1)[CH3:16]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 104392-AminopyridineHCID 233830Ethyl (2-chloroacetyl)carbamate

Product 1

HCID 11369557(7-Pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-carbamic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of aminopyridine (3) (0.94 g, 5.49 mmol), ethyl chloroacetylcarbamate (1.09 g, 6.58 mmol) and 2,6-lutidine (0.76 mL, 6.58 mmol) in 1,3-dimethyl-2-imidazolidinone (6 mL) was warmed under nitrogen at 110° C. for 4.5 hours. The mixture was diluted with EtOAc and washed with water (6 times), then adsorbed onto silica by removal of solvent in vacuo. The product was chromatographed on silica. Elution with EtOAc gave foreruns, while MeOH/EtOAc (2:23) eluted product (79 mg, 5%) as a solid, mp 248-252° C. (decomposed).

Workup

  1. washwashed with water (6 times)
  2. customadsorbed onto silica by removal of solvent in vacuo
  3. customThe product was chromatographed on silica
  4. washElution with EtOAc
  5. customgave foreruns
  6. washwhile MeOH/EtOAc (2:23) eluted product (79 mg, 5%) as a solid, mp 248-252° C. (decomposed)

Sources & evidence

ORD record
ord-f469de72a1b04053ad0ec9cf9f4a3816
Source dataset
uspto-grants-2009_07
Patent number
US07563788B2

Reaction notes

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