Pyridinium hydrochloride → HCID 22025332, compound

HRID 1792843Notes

Reaction equation

HRID 1792843 reaction equation
[C:1]1([S:7]([NH:10][CH:11]([CH2:25][C:26]2[CH:34]=[C:33]([Cl:35])[C:32]([O:36]C)=[C:31]3[C:27]=2[CH:28]=[N:29][NH:30]3)[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH+]1C=CC=CC=1>>[C:1]1([S:7]([NH:10][CH:11]([CH2:25][C:26]2[CH:34]=[C:33]([Cl:35])[C:32]([OH:36])=[C:31]3[C:27]=2[CH:28]=[N:29][NH:30]3)[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 22025325HCID 22025325, compound

Product 1

HCID 22025332HCID 22025332, compound

Procedure

2-Benzenesulfonylamino-3-(6-chloro-7-methoxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide (0.10 g, 0.19 mmol) and pyridinium hydrochloride (ca. 0.7 g) are combined in a 2 mL pressure vial. The reaction is heated to obtain a melt (ca. 170° C. bath). After 50 min. the reaction is cooled and partitioned between EtOAc and NH4Cl. The organic layer is washed with water, brine and dried over MgSO4. The solution is concentrated and purified by column chromatography (silica, 4% MeOH/CH2Cl2) to provide 2-benzenesulfonylamino-3-(6-chloro-7-hydroxy-1H-indazol-4-yl)-N-(4-phenyl-butyl)-propionamide.

Workup

  1. temperatureThe reaction is heated
  2. customto obtain
  3. custom(ca. 170° C. bath)
  4. temperatureAfter 50 min. the reaction is cooled
  5. custompartitioned between EtOAc and NH4Cl
  6. washThe organic layer is washed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationThe solution is concentrated
  9. custompurified by column chromatography (silica, 4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a1f2beba88ac49209805ebde323201bc
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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