Hydrochloric Acid → HCID 178441501, compound

HRID 1586838Notes

Reaction equation

HRID 1586838 reaction equation
[CH2:1]([C:5]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:25]=[C:24]([Cl:26])[S:23][C:22]=3[C:27]3[N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].Cl.[OH-].[Na+]>O1CCOCC1>[CH2:1]([C:5]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:25]=[C:24]([Cl:26])[S:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19759434HCID 19759434, compound

Product 1

HCID 178441501HCID 178441501, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Butyl-3-[4-[5-chloro-2-(1-trityl-1H-tetrazol-5-yl)-3-thienyl]benzyl]-3H-imidazo[4,5-b]pyridine (1.02 g) was dissolved in 1,4-dioxane (10 ml) and treated with 1N hydrochloric acid at ambient temperature for 10 hours. The reaction mixture was neutralized with 1N aqueous sodium hydroxide and concentrated in vacuo. The residue was extracted with dichloromethane-methanol (4:1) and the extract was evaporated in vacuo. The residue was purified by silica gel column chromatography to afford 2-butyl-3-[4-[5-chloro-2-(1H-tetrazol-5-yl)-3-thienyl]benzyl]-3H-imidazo[4,5-b]pyridine (640 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with dichloromethane-methanol (4:1)
  3. customthe extract was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-923e4720f9624b3db26aa7e8a17308d1
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

Loading…