Ammonium Chloride → HCID 178511957, compound

HRID 1622162Notes

Reaction equation

HRID 1622162 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-031a9fd26ae1484193c6b2a3502588f4
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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