Quinone → HCID 178475152, compound

HRID 1454558Notes

Reaction equation

HRID 1454558 reaction equation
[C:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:18]=2)[C:11]([OH:16])=[C:12]([CH:14]=O)[CH:13]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2].[NH2:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[NH2:37])[C:31]([NH2:33])=[NH:32].C1(=O)C=CC(=O)C=C1>CO>[C:1]([NH:4][S:5]([C:8]1[CH:13]=[C:12]([C:14]2[NH:37][C:36]3[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[NH:32])=[CH:29][C:28]=3[N:27]=2)[C:11]([OH:16])=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23](=[O:25])(=[O:24])[NH2:26])[CH:18]=2)[CH:9]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4650QuinoneHCID 109756643,4-DiaminobenzimidamideHCID 86607737N-acetyl 5-formyl-6-hydroxy-biphenyl-3,3'-disulfonamide

Product 1

HCID 178475152HCID 178475152, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-acetyl 5-formyl-6-hydroxy-biphenyl-3,3′-disulfonamide (74 mg, 0.19 mmol) was dissolved in methanol (10 mL)and stirred at room temperature. 3,4-Diaminobenzamidine (39 mg, 0.21 mmol) and 1,4-benzoquinone (20 mg, 0.2 mmol) were added to the solution and the mixture was refluxed for 1 hour. The solvent was removed by rotary evaporation under reduced pressure and the residue was dissolved in water and acetonitrile and purified by reverse phase HPLC (0.02N HCl/ACN) to give 2-(5-acetylsulfarnoyl-2-hydroxy-3′-sulfamoyl-biphenyl-3-yl)-1H-benzoimidazole-5-carboxamidine (14.1 mg) as a yellow amorphous powder. MS m/z: 527.4 (M−H+) and 529.3 (M+H+). 1H NMR (400 MHz, DMSO-d6): δ 9.36 (bs, 2H), 8.94 (bs, 2H), 8.08 (d, J=2.2 Hz, 1H), 8.22 (bs, 1H), 8.10 (t, J=1.5 Hz, 1H), 7.96 (d, J=2.2 Hz, 1H) 7.89 (d, J=1.8 Hz, 1H), 7.87-7.85 (m, 2H), 7.76 )dd, J=10, 1.5 Hz, 1H), 7.71 (t, J=7.7 Hz, 1H), 7.46 (s, 2H) and 1.96 (s, 3H).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customThe solvent was removed by rotary evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. customacetonitrile and purified by reverse phase HPLC (0.02N HCl/ACN)

Sources & evidence

ORD record
ord-a49eb9e2d68d471495fc8995f828bd13
Source dataset
uspto-grants-2009_01
Patent number
US07479502B2

Reaction notes

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