Water → HCID 22485113, compound

HRID 1368253Notes

Reaction equation

HRID 1368253 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1.N1C=CC=CC=1.[CH2:30]([S:34](Cl)(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33].O>ClCCl>[CH2:30]([S:34]([NH:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1)(=[O:36])=[O:35])[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 754301-Butanesulfonyl chlorideHCID 22388007HCID 22388007, compound

Product 1

HCID 22485113HCID 22485113, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (300 mg) in dichloromethane (3.0 ml) was added pyridine (143 mg). To this suspension was added 1-butanesulfonyl chloride (156 mg) under ice-cooling and the mixture was stirred for 5 min and at room temperature for 7 hr. Water was added to the reaction mixture and extracted twice with chloroform. The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. Methanol was added to the residue. The mixture was crystallized, collected by filtration, and dried under reduced pressure to give methyl 3-(4-(N-(1-butanesulfonyl)amino)-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate as ochroid crystals (287 mg).

Workup

  1. temperaturecooling
  2. extractionextracted twice with chloroform
  3. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. additionMethanol was added to the residue
  8. customThe mixture was crystallized
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-31d2942c18fb45b4bdb89a8244a34423
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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