Sodium Iodide → HCID 18695887, compound

HRID 1870240Notes

Reaction equation

HRID 1870240 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(C)=O>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][C:23]([NH:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[CH2:14][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:32]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amineHCID 53791088HCID 53791088, compound

Product 1

HCID 18695887HCID 18695887, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 8-amino-2,3-dimethylimidazo[1,2-a]-pyridine (0.58 g), 2-pyridinylmethyl (2-chloromethyl-3-methylphenyl)carbamate (1.04 g), sodium carbonate (0.95 g) and sodium iodide (0.2 g) in acetone (25 ml) is stirred at RT for 16 h. The precipitate is filtered off and washed with acetone, and the filtrate is concentrated on a rotary evaporator. The residue is taken up in sodium hydrogencarbonate solution (40 ml) and extracted with dichloromethane (3×40 ml). The combined organic extracts are washed with water (70 ml), dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: ethyl acetate). After concentration of the main fraction and crystallization from acetone, 0.4 g (27%) of the title compound of m.p. 163-165° C. is obtained.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with acetone
  3. concentrationthe filtrate is concentrated on a rotary evaporator
  4. extractionextracted with dichloromethane (3×40 ml)
  5. washThe combined organic extracts are washed with water (70 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography on silica gel (eluent: ethyl acetate)
  9. customAfter concentration of the main fraction and crystallization from acetone, 0.4 g (27%) of the title compound of m.p. 163-165° C.
  10. customis obtained

Sources & evidence

ORD record
ord-b627cc37a75e4aaca82899caab39ad55
Source dataset
uspto-grants-2000_08
Patent number
US06096758

Reaction notes

Loading…