Triethylamine → HCID 53983720, compound

HRID 1458424Notes

Reaction equation

HRID 1458424 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][N:15]2[C:19]3[CH:20]=[C:21]([NH:27][CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH:22]=[C:23]([C:24]([NH2:26])=[O:25])[C:18]=3[N:17]=[C:16]2[CH:34]([CH3:36])[CH3:35])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[CH2:37]([N:39](CC)CC)[CH3:38].C(OC(=N)C)C>CO>[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][N:15]2[C:19]3[CH:20]=[C:21]([N:27]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[C:37](=[NH:39])[CH3:38])[CH:22]=[C:23]([C:24]([NH2:26])=[O:25])[C:18]=3[N:17]=[C:16]2[CH:34]([CH3:36])[CH3:35])=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65066Ethyl acetimidateHCID 22100725HCID 22100725, compound

Product 1

HCID 53983720HCID 53983720, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(4-amidinonaphth-1-yl)methyl-2-isopropyl-4-aminocarbonyl-6-(piperidin-4-ylamino)benzimidazole (1 g) in methanol (50 mL) was added triethylamine (3 mL) and ethylacetimidate (1 g). After stirring for 3 hours, the reaction was concentrated. The residue was purified by HPLC on a C18 Dynamax column with a 3-25% acetonitrile in water gradient with 0.1% trifluoroacetic acid to afford 1-(4-amidinonaphth-1-yl)methyl-2-isopropyl-4-aminocarbonyl-6-(N-(1-iminoethyl)piperidin-4-ylamino)benzimidazole, 1H NMR (DMSO, 300 MHz) δ 9.70 (s, 2H), 9.58 (s, 2H), 9.40 (s, 1H), 9.35 (s, 1H), 8.82 (s, 1H), 8.62-7.20 (m, 9H), 6.10 (s, 2H), 4.10-3.50 (m, 6H), 2.50 (s, 3H), 2.26 (m, 2H), 1.70 (m, 2H), 1.60 (d, 6H), as white solid after freeze drying removal of the solvent.

Workup

  1. concentrationthe reaction was concentrated
  2. customThe residue was purified by HPLC on a C18 Dynamax column with a 3-25% acetonitrile in water gradient with 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-64af8bf5c23844d1a444aaf0acd42f2a
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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