Potassium Carbonate → HCID 178513235, compound

HRID 1858029Notes

Reaction equation

HRID 1858029 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:9]=2[N:8]=1.Cl.[NH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+]>CO>[OH:20][NH:19][C:16]([C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:8][C:9]=2[CH:15]=1)=[NH:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 178509507HCID 178509507, compound

Product 1

HCID 178513235HCID 178513235, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture comprising 2-pyridin-2-yl-1H-benzimidazole-5-carbonitrile (110 g, 0.5 mmol), hydroxylamine hydrochloride (38.2 mg, 0.55 mmol), potassium carbonate (104 mg, 0.75 mmol) and methanol (10 mL) was heated at reflux for 2.5 hours and then concentrated to dryness. The residue was taken up and purified by preparative reverse phase HPLC. The combined pure fractions were lyophilized to provide N-hydroxy-2-pyridin-2-yl-1H-benzimidazole-5-carboxamidine (40 mg, 0.23 mmol); 1H-NMR (300 Mhz, DMSO-d6): 7.53-7.57 (m, 2H), 7.80 (d, 1H), 8.01-8.04 (m, 2H), 8.32 (d, 1H), 8.75 (d, 1H), 9.20 (b, 2H); MS (ESI), Calculated for C13H11N5O: 253.1, Found (MH+): 253.7.

Workup

  1. temperatureat reflux for 2.5 hours
  2. concentrationconcentrated to dryness
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-a6b5f07bd9b84490b07186eaaa070661
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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