Hydrochloric Acid → HCID 178479777, compound

HRID 1292983Notes

Reaction equation

HRID 1292983 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([CH2:21][S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]([O-])=O.[Na+].[OH-].[Na+].[ClH:37]>O>[ClH:37].[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:17](=[CH:19][CH:20]=2)[NH:18][N:31]=[C:21]3[S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 589047884-(4-Benzylpiperazin-1-yl)-2-[(Phenylsulfonyl)methyl]aniline

Product 1

HCID 178479777HCID 178479777, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 4-(4-benzylpiperazin-1-yl)-2-[(phenylsulfonyl)methyl]-aniline (0.371 g, 0.88 mmol) in 4.0 M aqueous hydrochloric acid is cooled in an ice bath, treated dropwise with NaNO2 (91 mg, 1.32 mmol) in water, stirred for 40 min, treated with 2.5 M aqueous NaOH to pH ˜14 and filtered. The filtercake is dissolved in CH2Cl2, and chromatographed (silica gel, ethyl acetate as eluent) to afford the free indazole of the title product as a yellow solid (276 mg, 64%). The solid is dissolved in a mixture of ethanol and CH2Cl2, treated with 4.0 M HCl in dioxane, and concentrated in vacuo to give a solid residue. The residue is triturated with ethyl acetate to afford the title product as an off-white solid, 278 mg (57% yield), mp 177–180° C., identified by NMR and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. dissolutionThe filtercake is dissolved in CH2Cl2
  3. customchromatographed (silica gel, ethyl acetate as eluent)

Sources & evidence

ORD record
ord-551828ddb12e47188bae0ea4aef06c8d
Source dataset
uspto-grants-2007_07
Patent number
US07238696B2

Reaction notes

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