Hydrochloric Acid → HCID 178511937, compound

HRID 1622158Notes

Reaction equation

HRID 1622158 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]([C:20]2[NH:24][N:23]=[N:22][N:21]=2)=[CH:4][C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][NH2:32])[C:26]=1[OH:33].C(N(CC)CC)C.[O-:41][C:42]#[N:43].[K+].Cl>CO>[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]([C:20]2[NH:24][N:23]=[N:22][N:21]=2)=[CH:4][C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][NH:32][C:42]([NH2:43])=[O:41])[C:26]=1[OH:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11378442Potassium cyanateHCID 178511936HCID 178511936, compound

Product 1

HCID 178511937HCID 178511937, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2-(2,2′-Dihydroxy-5-(1H-tetrazol-5-yl)-3′-aminomethylbiphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.2 g 0.2 mmol), prepared as in Example 7, was dissolved in methanol (10 mL). The solution was treated with triethylamine (0.2 mL, 1.5 mmol) and then potassium cyanate (0.09 g, 1.1 mmol aqueous solution, 0.5 mL) was added in 3 portions over 1 hour. 1N hydrochloric acid (5 mL) was added and the mixture was stirred at 50° C. over 3 days. Drying afforded crude product, which was subjected to purification by reverse phase HPLC to give 2-(2,2′-dihydroxy-5-(1H-tetrazol-5-yl)-3′-ureidomethylbiphenyl-3-yl]-1H-benzoimidazole-5-carboxamidine (0.008 g) as a brown solid. LCMS calcd. 484.47, obsrvd. (M+H) 485.1, (M−H) 483.1.

Workup

  1. customDrying
  2. customafforded crude product, which
  3. customwas subjected to purification by reverse phase HPLC

Sources & evidence

ORD record
ord-ebfecef2c948479a96bf3dee1fa20271
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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