Quinone → HCID 178511952, compound

HRID 1752933Notes

Reaction equation

HRID 1752933 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][S:12]([C:15]2[CH:16]=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[OH:30])[C:18]([OH:23])=[C:19]([CH:21]=O)[CH:20]=2)(=[O:14])=[O:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[NH2:42])[C:36]([NH2:38])=[NH:37].C1(=O)C=CC(=O)C=C1>C(O)C>[OH:23][C:18]1[C:19]([C:21]2[NH:42][C:41]3[CH:40]=[CH:39][C:35]([C:36]([NH2:38])=[NH:37])=[CH:34][C:33]=3[N:32]=2)=[CH:20][C:15]([S:12]([NH:11][C:9](=[O:10])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:13])=[O:14])=[CH:16][C:17]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[OH:30]

Participants

5

Reactant 3

HCID 4650QuinoneHCID 221255323,4-Diaminobenzimidamide hydrochlorideHCID 86607738N-(3-Phenylpropionyl)-5-formyl-6,2'-dihydroxy-biphenyl-3-sulfonamide

Product 1

HCID 178511952HCID 178511952, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Phenylpropionyl)-5-formyl-6,2′-dihydroxy-biphenyl-3-sulfonamide (0.065 g, 0.15 mmol), prepared as in Reference 22, 3,4-diaminobenzamidine hydrochloride (0.043 g 0.23 mmol) and benzoquinone (0.018 g, 0.16 mmol) were combined in ethanol (15 mL) and the mixture was heated under reflux for 1 hour. The solvent was evaporated in vacuum and the product was purified from the residue by reverse phase HPLC (acetonitrile/0.02N HCl gradient) to give 2-[2,2′-dihydroxy-5-(3-phenylpropionylaminosulfonyl)biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.033 g). 1H NMR (DMSO-d6): δ 2.50 (t, J=7.7 Hz, 2H), 2.63 (t, J=7.7 Hz, 2H), 6.82-7.22 (m, 9H), 7.72 (dd, J1=9.2 Hz, J2=1.7 Hz, 1H), 7.78 (d, J=2.5 Hz, 1H), 7.84 (d, J=9.2 Hz, 1H), 8.18 (s, 1H), 8.68 (d, J=2.5 Hz, 1H), 8.99 (s, 2H), 9.34 (s, 2H), 12.06 (s, 1H). MS. found (M+H+) 556.4, (M−H+) 554.4, calc 555.16.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was evaporated in vacuum
  4. customthe product was purified from the residue by reverse phase HPLC (acetonitrile/0.02N HCl gradient)

Sources & evidence

ORD record
ord-c75342085fb54b3e9c0d7e7706c1d83d
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

Loading…