Triethylamine → HCID 178511955, compound

HRID 1622163Notes

Reaction equation

HRID 1622163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([S:14](=[O:27])(=[O:26])[NH:15][C:16](=[O:25])[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:11]=[C:10]([C:28]3[NH:32][C:31]4[CH:33]=[CH:34][C:35]([C:37]([NH2:39])=[NH:38])=[CH:36][C:30]=4[N:29]=3)[C:9]=2[OH:40])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[O-:48][C:49]#[N:50].[K+]>CO.O>[OH:40][C:9]1[C:10]([C:28]2[NH:32][C:31]3[CH:33]=[CH:34][C:35]([C:37]([NH2:39])=[NH:38])=[CH:36][C:30]=3[N:29]=2)=[CH:11][C:12]([S:14](=[O:27])(=[O:26])[NH:15][C:16](=[O:25])[CH2:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:49]([NH2:50])=[O:48])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11378442Potassium cyanateHCID 178511953HCID 178511953, compound

Product 1

HCID 178511955HCID 178511955, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-[3′-Amino-2-hydroxy-5-(3-pyridin-3-yl-propionylsulfamoyl)-biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.015 g, 0.023 mmol), prepared as in Example 10, was dissolved in a mixture of methanol and water and then triethylamine was added to bring the solution to pH 9. The mixture was heated with potassium cyanate (0.018 g, 0.23 mmol) for 12 hour at 40° C., concentrated by evaporation under reduced pressure and the crude product was purified by reversed phase HPLC (acetonitrile gradient) to give 2-[2-hydroxy-5-(3-pyridin-3-yl-propionylsulfamoyl)-3′-ureido-biphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.01 g). MS: found (M+H+) 599.5, (M−H+) 597.7, calc. 598.17.

Workup

  1. concentrationconcentrated by evaporation under reduced pressure
  2. customthe crude product was purified by reversed phase HPLC (acetonitrile gradient)

Sources & evidence

ORD record
ord-4982d6935b9441089d4c87e75cc8b332
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

Loading…