Triethylamine → ethyl 2-[[(2R)-2-[1-methyl-2-[[4-[N-(4-methylbenzoyl)carbamimidoyl]anilino]methyl]benzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

HRID 1357801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357801
Cl.Cl.[C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:22]([C@@:24]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])([C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:27])[CH3:25])=[CH:23][C:16]=3[N:15]=2)=[CH:8][CH:7]=1)(=[NH:5])[NH2:4].C(N(CC)CC)C.[CH3:47][C:48]1[CH:65]=[CH:64][C:51]([C:52](OC2C=CC([N+]([O-])=O)=CC=2)=[O:53])=[CH:50][CH:49]=1>C(Cl)Cl>[CH3:47][C:48]1[CH:65]=[CH:64][C:51]([C:52]([NH:5][C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][C:22]([C@@:24]([NH:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])([C:26]([N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[O:27])[CH3:25])=[CH:23][C:16]=4[N:15]=3)=[CH:8][CH:7]=2)=[NH:4])=[O:53])=[CH:50][CH:49]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 532509p-Toluic acid, 4-nitrophenyl esterHCID 23381735(r)-2-(4-Amidinophenylaminomethyl)-1-methyl-5-[1-(ethoxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole-dihydrochloride

Produkt 1

HCID 145816426ethyl 2-[[(2R)-2-[1-methyl-2-[[4-[N-(4-methylbenzoyl)carbamimidoyl]anilino]methyl]benzimidazol-5-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]amino]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of 0.7 g (1.2 mmol) of (R)-2-(4-amidinophenylaminomethyl)-1-methyl-5-[1-(ethoxycarbonylmethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole-dihydrochloride in 25 ml of methylene chloride is combined with 4.0 ml (28 mmol) of triethylamine and 0.8 g (3.0 mmol) of 4-nitrophenyl 4-methyl-benzoate and heated to 50° C. for 3.5 hours, whereupon a clear solution is formed. After cooling, it is washed with sodium bicarbonate solution, saline solution and water, dried over magnesium sulphate and concentrated by evaporation. The crude product is purified on silica gel, eluting with ethyl acetate/ethanol (50:1 and 9:1). The uniform fractions are combined, concentrated by evaporation, triturated with ether, suction filtered and dried.

Aufarbeitung

  1. customis formed
  2. temperatureAfter cooling
  3. washit is washed with sodium bicarbonate solution, saline solution and water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe crude product is purified on silica gel
  7. washeluting with ethyl acetate/ethanol (50:1 and 9:1)
  8. concentrationconcentrated by evaporation
  9. customtriturated with ether, suction
  10. filtrationfiltered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b94f5f00f196485696769696d4db5805
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593355B2

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