Triethylamine → HCID 10128398, compound

HRID 2109995Notes

Reaction equation

HRID 2109995 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([NH2:17])[C:11]=2[N:10]=[C:9]1[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.C(N(CC)CC)C.[CH2:42]([S:45](Cl)(=[O:47])=[O:46])[CH2:43][CH3:44].O1CCOCC1.Cl>O1CCCC1>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[CH2:26][N:23]1[CH2:22][CH2:21][CH:20]([CH2:19][NH:18][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][S:45]([CH2:42][CH2:43][CH3:44])(=[O:47])=[O:46])[C:11]=3[N:10]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 204431481,4-Dioxane hydrochlorideHCID 69070206HCID 69070206, compound

Product 1

HCID 10128398HCID 10128398, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 4-amino-2-{[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-amino}-benzimidazole-1-carboxylic acid tert-butyl ester (10 mg, 0.02 mmol) in tetrahydrofuran (1 ml), triethylamine (0.04 mmol) and propane-1-sulfonyl chloride (0.08 mmol) were added and the mixture was stirred at room temperature overnight. After adding a 4N hydrogen chloride-1,4-dioxane solution (1 ml) to the reaction mixture, it was stirred at 50° C. for 1 hour. The solvent was removed under reduced pressure, dichloromethane and 5N aqueous sodium hydroxide were added to the obtained residue, and after stirring, the organic layer was passed through SCX (Bond Elute SCX500MG). The SCX was washed with methanol and elution was performed with a 2N ammonia-methanol solution. The solvent was distilled off under reduced pressure to obtain propane-1-sulfonic acid (2-{[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazol-4-yl)-amide. The compound was identified by LC-MS.

Workup

  1. additionwere added
  2. stirringwas stirred at 50° C. for 1 hour
  3. customThe solvent was removed under reduced pressure, dichloromethane and 5N aqueous sodium hydroxide
  4. additionwere added to the obtained residue
  5. stirringafter stirring
  6. washthe organic layer was passed through SCX (Bond Elute SCX500MG)
  7. washThe SCX was washed with methanol and elution
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4fae77e3bd494e2e9748b702e527c520
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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