Ammonia → HCID 57749441, compound

HRID 1162478Notes

Reaction equation

HRID 1162478 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:15]([Cl:21])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=O)[CH3:2].[CH3:22][NH2:23].[BH4-].[Na+].N>CCO.CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[Br:20][C:18]1[CH:19]=[C:14]([NH:13][S:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([NH:23][CH3:22])[CH3:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[C:15]([Cl:21])=[N:16][CH:17]=1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 595195144-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide

Product 1

HCID 57749441HCID 57749441, compoundYield 87%

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide (540.2 mg, 1.386 mmol) was suspended in EtOH (5.0 mL) and titanium (IV) isopropoxide (0.82 mL, 2.8 mmol) and methylamine (4.2 mL, 8.4 mmol, 2.0 M in THF) were added. The reaction was stirred at room temperature overnight. Then, sodium borohydride (95.7 mg, 2.53 mmol) was added, and the reaction was stirred at room temperature for 30 minutes, and then water (10 mL) and ca. 7 N ammonia in MeOH (2.9 mL) were added simultaneously via syringe, causing precipitation. The reaction was stirred at room temperature, and after 45 minutes, the reaction contents were filtered. The solid was washed with EtOAc and MeOH, and the filtrate was concentrated and purified using silica gel with 20:1 DCM/MeOH to 3:1 DCM/2 N ammonia in MeOH to afford N-(5-bromo-2-chloropyridin-3-yl)-4-(1-(methylamino)ethyl)benzenesulfonamide (488 mg, 87% yield). MS (ESI positive ion) m/z: 404 (M+1, 79Br), 406 (M+1, 81Br). Calcd. for C14H15BrClN3O2S: 403 (79Br), 405 (81Br).

Workup

  1. stirringthe reaction was stirred at room temperature for 30 minutes
  2. customprecipitation
  3. stirringThe reaction was stirred at room temperature
  4. waitafter 45 minutes
  5. customthe reaction contents
  6. filtrationwere filtered
  7. washThe solid was washed with EtOAc and MeOH
  8. concentrationthe filtrate was concentrated
  9. custompurified

Sources & evidence

ORD record
ord-7da520d294124525b5355af88f0a620d
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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