4-Pyridinemethanamine → HCID 178479302, compound

HRID 1454555Notes

Reaction equation

HRID 1454555 reaction equation
[ClH:1].[C:2]([C:5]1[CH:31]=[CH:30][C:8]2[NH:9][C:10]([C:12]3[CH:13]=[C:14]([C:27](O)=[O:28])[CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[OH:26])[C:17]=3[OH:18])=[N:11][C:7]=2[CH:6]=1)(=[NH:4])[NH2:3].Cl.CN(C)CCCN=C=NCC.[NH2:44][CH2:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1>CN(C)C=O>[ClH:1].[C:2]([C:5]1[CH:31]=[CH:30][C:8]2[NH:9][C:10]([C:12]3[CH:13]=[C:14]([C:27]([NH:44][CH2:45][C:46]4[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=4)=[O:28])[CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[OH:26])[C:17]=3[OH:18])=[N:11][C:7]=2[CH:6]=1)(=[NH:4])[NH2:3]

Participants

5

Reactant 3

HCID 773174-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178479304HCID 178479304, compound

Product 1

HCID 178479302HCID 178479302, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(5-carbamimidoyl-1H-benzoimidazol-2-yl)-5′-fluoro-6,2′-dihydroxy-biphenyl-3-carboxylic acid hydrochloride (100 mg, 0.226 mmol), prepared as in Reference 23, O-(7-azabenzotrizol-1-yl)-1,2,3,3-tetramethyluroniumhexafluorophosphate monohydrate (37 mg, 0.242 mmol) and (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride (46 mg, 0.237 mmol) were dissolved in anhydrous N,N-dimethylformamide (10 mL). The mixture was stirred at room temperature for 1 hour and then 4-aminomethylpyridine (27 mg, 0.248 mmol) was added to the mixture. The mixture was stirred at ambient temperature for 18 hours and then concentrated to a gum under high vacuum. The residue was dissolved in 5% acetonitrile/95% 20 mM hydrochloric acid (10 mL) and product purified via preparative C18 reverse phase HPLC (5% to 35% acetonitrile gradient, 20 mM HCl aqueous to give 5-(5-carbamimidoyl-1H-benzoimidazol-2-yl)-5′-fluoro-6,2′-dihydroxy-N-pyridin-4-ylmethyl-biphenyl-3-carboxamide hydrochloride (50 mg) as a tan powder.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 18 hours
  2. concentrationconcentrated to a gum under high vacuum
  3. dissolutionThe residue was dissolved in 5% acetonitrile/95% 20 mM hydrochloric acid (10 mL)
  4. customproduct purified via preparative C18 reverse phase HPLC (5% to 35% acetonitrile gradient, 20 mM HCl aqueous

Sources & evidence

ORD record
ord-2bb643a61da240df80a2ccf6a7ee4013
Source dataset
uspto-grants-2009_01
Patent number
US07479502B2

Reaction notes

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