Hydrochloric Acid → HCID 22485157, compound

HRID 1368267Notes

Reaction equation

HRID 1368267 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([N:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([OH:16])=O)=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:17].C(N1C=CN=C1)(N1C=CN=C1)=O.[Na].[CH:42]([S:47]([NH2:50])(=[O:49])=[O:48])=[CH:43][CH2:44][CH2:45][CH3:46].Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:21]=[C:20]([N:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14](=[O:16])[NH:50][S:47](/[CH:42]=[CH:43]/[CH2:44][CH2:45][CH3:46])(=[O:49])=[O:48])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 22485044HCID 22485044, compoundHCID 86589526HCID 86589526, compound

Product 1

HCID 22485157HCID 22485157, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-Chloro-4-(N-ethoxycarbonyl-N-methylamino)benzyl)-2-methyl-3H-imidazo[4, 5-b]pyridine-5-carboxylic acid (150 mg) was dissolved in dry N,N-dimethylformamide (1.5 ml), and carbonyldiimidazole (91 mg) was added, which was followed by stirring at room temperature for 1.5 hr. To the reaction mixture was added 1-penten-1-ylsulfonamide sodium salt (96 mg) and the mixture was stirred at room temperature for 7 hr. 1N Hydrochloric acid was added dropwise under ice-cooling to adjust to pH 4. Water (1.5 ml) was added and the mixture was applied to ultrasonic washer for 15 min and then stirred for 15 min. The precipitate was collected by filtration, washed with water, suspended in ethanol (0.5 ml), heated in a boiling bath and stirred at room temperature for 30 min. The precipitate was collected by filtration, washed with ethanol, and recrystallized from N,N-dimethylformamide and water to give 3-(2-chloro-4-(N-ethoxycarbonyl-N-methylamino)benzyl)-2-methyl-5-((E)-1-penten-1-ylsulfonylcarbamoyl)-3H-imidazo[4,5-b]pyridine (165 mg) as colorless crystals. m.p.: 165-166° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 7 hr
  2. temperaturecooling
  3. waitthe mixture was applied to ultrasonic washer for 15 min
  4. stirringstirred for 15 min
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. temperatureheated in a boiling bath
  8. stirringstirred at room temperature for 30 min
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with ethanol
  11. customrecrystallized from N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-d5937b7eee184a1cac0ead2ec08e688e
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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