Pyridine → HCID 22485221, compound

HRID 1368266Notes

Reaction equation

HRID 1368266 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([NH:30][CH3:31])[CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14](=[O:24])[NH:15][S:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:18])=[O:17])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:25].N1C=CC=CC=1.[C:38](Cl)(=[O:42])[O:39][CH2:40][CH3:41]>ClCCl>[CH2:40]([O:39][C:38]([N:30]([C:28]1[CH:27]=[CH:26][C:3]([CH2:4][N:5]2[C:9]3=[N:10][C:11]([C:14](=[O:24])[NH:15][S:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:17])=[O:18])=[CH:12][CH:13]=[C:8]3[N:7]=[C:6]2[CH3:25])=[C:2]([Cl:1])[CH:29]=1)[CH3:31])=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22485111HCID 22485111, compound

Product 1

HCID 22485221HCID 22485221, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(2-chloro-4-(methylamino)benzyl)-2-methyl-5-(1-pentanesulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (278 mg) in dichloromethane (3 ml) were added pyridine (148 mg) and ethyl chlorocarbonate (129 mg) under ice-cooling, and the mixture was stirred for 24 hr. The solvent was evaporated and the residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give 3-(4-(N-(ethoxycarbonyl)-N-methylamino)-2-chlorobenzyl)-2-methyl-5-(1-pentanesulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (126 mg) as a white powder.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate)
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4112901995644ea1ab8a862498f0aeba
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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