Ammonium Chloride → HCID 178509264, compound

HRID 337915Notes

Reaction equation

HRID 337915 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[C:15]2[C:16]([N+:20]([O-])=O)=[N:17][NH:18][CH:19]=2)[CH:5]=[C:4]([F:23])[C:3]=1[S:24]([NH:27][C:28]1[N:29]=[CH:30][S:31][CH:32]=1)(=[O:26])=[O:25].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:20][C:16]1[C:15]([C@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]2[O:8][C:6]2[CH:5]=[C:4]([F:23])[C:3]([S:24]([NH:27][C:28]3[N:29]=[CH:30][S:31][CH:32]=3)(=[O:25])=[O:26])=[C:2]([F:1])[CH:7]=2)=[CH:19][NH:18][N:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 178526906HCID 178526906, compound

Product 1

HCID 178509264HCID 178509264, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the 2,6-difluoro-4-{[(1S*,2R*)-2-(3-nitro-1H-pyrazol-4-yl)cyclohexyl]oxy}-N-(1,3-thiazol-4-yl)benzenesulfonamide (167 mg, 0.343 mmol) prepared in Example 116c in ethanol (4.0 mL) and water (2.0 mL), ammonium chloride (92.0 mg, 1.72 mmol) and an iron powder (57.6 mg, 1.03 mol) were added, and the reaction solution was stirred for 2 hours under heated reflux. After allowing to cool, the reaction solution was filtered through celite, the filtrate was vacuum concentrated, and the residue was purified with silica gel chromatography (dichloromethane/methanol=93:7) to yield the title compound (145 mg, 92%) as a colorless solid.

Workup

  1. temperatureunder heated
  2. temperaturereflux
  3. temperatureto cool
  4. filtrationthe reaction solution was filtered through celite
  5. concentrationconcentrated
  6. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=93:7)

Sources & evidence

ORD record
ord-a14a69d4f9af4fc7ad9f370e0fffeb91
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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