Triethylamine → HCID 178511955, compound

HRID 1752935Notes

Reaction equation

HRID 1752935 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-831f0f30a60a4cc2b89a7cbffa1ed3b2
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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