Pyridine → HCID 22485177, compound

HRID 1368255Notes

Reaction equation

HRID 1368255 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:24]=[C:23]([NH:25][CH3:26])[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20].N1C=CC=CC=1.[C:33](Cl)(=[O:37])[O:34][CH2:35][CH3:36]>O1CCCC1>[Cl:3][C:4]1[CH:24]=[C:23]([N:25]([C:33]([O:34][CH2:35][CH3:36])=[O:37])[CH3:26])[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22485098HCID 22485098, compound

Product 1

HCID 22485177HCID 22485177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-(2-chloro-4-(methylamino)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate dihydrochloride (418 mg), pyridine (396 mg) and tetrahydrofuran (4.2 ml) was added dropwise ethyl chlorocarbonate (0.115 ml) under ice-cooling and the mixture was stirred at room temperature for 6 hr. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was pulverized in diethyl ether to give methyl 3-(2-chloro-4-(N-ethoxycarbonyl-N-methylamino)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (340 mg) as a white powder.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0f173fba13c643b58047ae6fd560b8f5
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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