Hydrochloric Acid → HCID 178478039, compound

HRID 1404681Notes

Reaction equation

HRID 1404681 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][S:5][C:6]1[CH:27]=[CH:26][C:9]2[N:10](C(OC(C)(C)C)=O)[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:12][C:8]=2[CH:7]=1.ClC1C=CC=CC=1CSC1C=CC2N=C(C3C=CC=CN=3)N(C(OC(C)(C)C)=O)C=2C=1.Cl.O1CCOCC1>CO>[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][S:5][C:6]1[CH:27]=[CH:26][C:9]2[NH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:12][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67174260HCID 67174260, compoundHCID 68315013HCID 68315013, compound

Product 1

HCID 178478039HCID 178478039, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To stirred solution of tert-butyl 5-(2-chlorobenzylthio)-2-(pyridin-2-yl)-1H-benzo[d]imidazole-1-carboxylate (or the isomer, tert-butyl 6-(2-chlorobenzylthio)-2-(pyridin-2-yl)-1H-benzo[d]imidazole-1-carboxylate) (18 mg, 0.04 mmol) in methanol (2 mL) was added 4M HCl in dioxane (1 mL, 4 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue was purified by reverse phase preparative HPLC to give 5-(2-chlorobenzylthio)-2-(pyridin-2-yl)-1H-benzo[d]imidazole (2TFA) (8.8 mg, 38%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-aef1e02080114d35a4d0ca8cabf412e0
Source dataset
uspto-grants-2014_12
Patent number
US08912336B2

Reaction notes

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