HCID 178511956, compound → HCID 178511954, compound

HRID 1622164Notes

Reaction equation

HRID 1622164 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:33])(=[O:32])[NH:21][C:22](=[O:31])[CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:4][C:3]=1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([N+:40]([O-])=O)[CH:35]=1>FC(F)(F)C(O)=O.O=[Pt]=O>[NH2:40][C:36]1[CH:35]=[C:34]([C:3]2[CH:4]=[C:5]([S:20](=[O:33])(=[O:32])[NH:21][C:22](=[O:31])[CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]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:39]=[CH:38][CH:37]=1

Participants

4

Reactant 1

HCID 178511956HCID 178511956, compound

Product 1

HCID 178511954HCID 178511954, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

2-[2-Hydroxy-3′-nitro-5-(3-pyridin-3-yl-propionylsulfamoyl)-biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.031 g, 0.05 mMol), prepared as in Example 10, was dissolved in trifluoroacetic acid (5 mL) and the solution was subjected to hydrogenation at 50 psi over PtO2 catalyst for 12 hours. The mixture was concentrated in vacuum and product was purified from the residue by reverse phase HPLC (acetonitrile gradient) to give 2-[3′-amino-2-hydroxy-5-(3-piperidin-3-yl-propionylsulfamoyl)-biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.01 g). MS: found (M+H+) 562.4, (M−H+) 560.6, calc. 561.22.

Workup

  1. concentrationThe mixture was concentrated in vacuum and product
  2. customwas purified from the residue by reverse phase HPLC (acetonitrile gradient)

Sources & evidence

ORD record
ord-5c56c3d31d4746139a79c7ab6dd842c2
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

Loading…