Ammonium Chloride → HCID 58934070, compound

HRID 854395Notes

Reaction equation

HRID 854395 reaction equation
[NH2:1][C:2]1[C:3]([CH2:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.O.[C:32]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(OCC)OCC.O(C(C)(C)C)[K].[NH4+].[Cl-].C([O-])(O)=O.[Na+]>ClCCCl.C1COCC1.CCOC(C)=O.O>[CH2:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[N:4]=[C:3]3[C:21]([S:22]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)(=[O:24])=[O:23])=[CH:32][NH:1][C:2]3=[CH:7][CH:6]=2)[CH2:13][CH2:12]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

11

Reactant 6

HCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58934068HCID 58934068, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 58934070HCID 58934070, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 3-amino-6-(4-benzylpiperazin-1-yl)-2-[(phenylsulfonyl)-methyl]pyridine (1.41 g, 3.34 mmol), p-toluenesulfonic acid monohydrate (63 mg, 0.33 mmol), triethyl orthoformate (2.78 mL, 16.7 mmol) in 1,2-dichloroethane is heated at reflux temperature under nitrogen for 7.5 h, stirred at room temperature for 16 h and in vacuo to afford an oil residue. The residue is stirred in dry THF, treated with 1.0M KO-t-Bu in THF (4.35 mL, 4.35 mmol) for 2 h, treated sequentially with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and water and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a yellow solid residue. This residue is chromatograped (silica gel, EtOAc as eluent to afford the title compound as a pale yellow solid, 1.18 g (79% yield), mp 238-239° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureat reflux temperature under nitrogen for 7.5 h
  2. customto afford an oil residue
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid residue

Sources & evidence

ORD record
ord-17ce690c5484401d956650245733c24f
Source dataset
uspto-grants-2007_08
Patent number
US07259165B2

Reaction notes

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