Sodium Iodide → HCID 18695897, compound

HRID 1870241Notes

Reaction equation

HRID 1870241 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:33])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(C)=O>[OH:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=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:33]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amineHCID 54441959HCID 54441959, compound

Product 1

HCID 18695897HCID 18695897, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (0.63 g), 3-hydroxybenzyl (2-chloromethyl-3-methylphenyl)carbamate (1.2 g), sodium carbonate (1 g) and sodium iodide (0.14 g) in acetone (20 ml) is stirred at RT for 16 h. The precipitate is filtered off, washed with acetone and concentrated. 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, dried over sodium sulfate and concentrated. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 13:1). After concentration of the main fraction and crystallization from acetone, 0.4 g (22%) of the title compound of m.p. 190-193° C. is obtained.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with acetone
  3. concentrationconcentrated
  4. extractionextracted with dichloromethane (3×40 ml)
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 13:1)
  9. customAfter concentration of the main fraction and crystallization from acetone, 0.4 g (22%) of the title compound of m.p. 190-193° C.
  10. customis obtained

Sources & evidence

ORD record
ord-e7376b773688462bb14cd854a5b2ce80
Source dataset
uspto-grants-2000_08
Patent number
US06096758

Reaction notes

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