Benzylamine → 6-(5-amidino-1H-benzimidazol-2-yl)-N-benzylpyridine-4-carboxamide

HRID 1858026Notes

Reaction equation

HRID 1858026 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([C:12]3[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][N:13]=3)[NH:9][C:8]=2[CH:21]=1)(=[NH:3])[NH2:2].C1C=CC2N(O)N=NC=2C=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH2:72]([NH2:79])[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>C(#N)C.CCOCC.CN(C=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:11][C:10]([C:12]3[N:13]=[CH:14][CH:15]=[C:16]([C:18]([NH:79][CH2:72][C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)=[O:20])[CH:17]=3)=[N:9][C:8]=2[CH:21]=1)(=[NH:3])[NH2:2]

Participants

9

Reactant 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2724699PyBOPHCID 22125556HCID 22125556, compound

Product 1

HCID 1785119476-(5-amidino-1H-benzimidazol-2-yl)-N-benzylpyridine-4-carboxamideYield 33.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture comprising 2-(6-amidino-1H-benzimidazol-2-yl)pyridine-4-carboxylic acid (0.02 g, 0.06 mmol), HOBT (0.008 g, 0.07 mmol), PyBOP (0.032 g, 0.07 mmol), DMF (0.5 mL) and N-methylmorpholine (0.013 mL, 0.12 mmol) was shaken for 10 minutes and then benzyl amine (13 μL, 0.12 mmol) was added. The mixture was shaken for approximately 12 hours and combined with a mixture comprising ether and acetonitrile (5 mL) to give a precipitate. The precipitate was isolated by filtration and purified by HPLC to provide 6-(5-amidino-1H-benzimidazol-2-yl)-N-benzylpyridine-4-carboxamide (10 mg, 0.02 mmol); 1H-NMR (300 Mhz, DMSO-d6): 4.5 (d, 2H, J=5.5 Hz), 7.3 (m, 5H), 7.7 (m, 2H), 8.0 (dd, 1H), 8.2 (bs, 1H), 8.8 (s, 1H), 8.9 (m, 3H), 9.3 (s, 2H), 9.6 (t, 1H, J=1.5 Hz); MS (ESI), Calculated for C21H18N6O: 370.4, Found (MH+): 371.1.

Workup

  1. customto give a precipitate
  2. customThe precipitate was isolated by filtration
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-95f16ffb321b4817ac9e6da0a964f2f1
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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