Ammonium Chloride → HCID 178511957, compound

HRID 2069982Notes

Reaction equation

HRID 2069982 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[NH:18])=[CH:16][C:10]=3[N:9]=2)=[CH:6][C:5]([S:20](=[O:34])(=[O:33])[NH:21][C:22](=[O:32])[CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:3]=1[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-])=O)[CH:36]=1.[Cl-].[NH4+]>CO.[Fe]>[NH2:41][C:37]1[CH:36]=[C:35]([C:3]2[CH:4]=[C:5]([S:20](=[O:34])(=[O:33])[NH:21][C:22](=[O:32])[CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:6]=[C:7]([C:8]3[NH:12][C:11]4[CH:13]=[CH:14][C:15]([C:17]([NH2:19])=[NH:18])=[CH:16][C:10]=4[N:9]=3)[C:2]=2[OH:1])[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 178511958HCID 178511958, compound

Product 1

HCID 178511957HCID 178511957, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

2-[2-Hydroxy-3′-nitro-5-(4-phenyl-butyrylsulfamoyl)-biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.063 g, 0.1 mmol), prepared as in Example 10 was dissolved in methanol (3 mL) and saturated aqueous ammonium chloride (1 mL) was added to the solution. The mixture was heated with iron powder (1 g) for 5-10 minutes, filtered through celite and concentrated under reduced pressure. Product was purified from the residue by reverse phase HPLC (acetonitrile gradient) to give 2-[3′-amino-2-hydroxy-5-(4-phenyl-butyrylsulfamoyl)-biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.017 g). MS: found (M+H+) 569.3, (M−H+) 567.4, calc. 568.19.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customProduct was purified from the residue by reverse phase HPLC (acetonitrile gradient)

Sources & evidence

ORD record
ord-25bbae5c65274409a988cab65ca5ea35
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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