Hydrochloric Acid → HCID 69207392, compound

HRID 2252067Notes

Reaction equation

HRID 2252067 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:35](C(OCC)=O)[CH3:36])[N:19]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:42])(=[O:6])=[O:5])([CH3:3])[CH3:2].Cl.[OH-:44].[Na+]>C(O)C.O>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH2:35][CH2:36][C:27]([O:28][CH2:29][CH3:30])=[O:44])[N:19]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[C:20]=3[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:42])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69208534HCID 69208534, compound

Product 1

HCID 69207392HCID 69207392, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-isopropylsulfonyl-2-amino-6-(1-(trimethylsilylethoxymethyl)-2-(1-(ethoxycarbonyl)ethyl)-5-(phenyl)-imidazol-4-yl)-benzimidazole (91 mg, 0.14 mmol) in ethanol (3 mL) add HCl (37%, 3 mL) and stir at room temperature for 24 hours. Then, dilute the mixture with water (10 mL) and add a solution of NaOH (15%) until pH=6-7. Extract the mixture with EtOAc (3×30 mL) and dry (MgSO4) the combined organic layers and concentrate int vacuo. Purify the residue by HPLC to give 1-isopropylsulfonyl-2-amino-6-(1-(trimethylsilylethoxymethyl)-2-(ethoxycarbonylethyl)-5-(phenyl)-imidazol-4-yl)-benzimidazole as a white solid, 11 mg, 16% yield. FIA MS(ES+): m/z=482 (M+H)+. 1-Isopropylsulfonyl-6-(2-(2-carboxyethyl)-5-(phenyl)-imidazol-4-yl)-benzimidazole as a white solid is also obtained, 3 mg, 5% yield. MS (ES+): m/z=454 (M+H)+

Workup

  1. extractionExtract the mixture with EtOAc (3×30 mL)
  2. dry with materialdry (MgSO4) the combined organic layers
  3. concentrationconcentrate int vacuo
  4. customPurify the residue by HPLC

Sources & evidence

ORD record
ord-c617a94d5869453f952748be26af0123
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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