Isopropanol → [1-(2-Amino-3-carbamoyl-phenylcarbamoyl)-cyclohexyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 12633

Reaktionsgleichung

Reaktionsgleichung von HRID 12633
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3([C:25](O)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.Cl.[NH2:42][C:43]1[C:51]([NH2:52])=[CH:50][CH:49]=[CH:48][C:44]=1[C:45]([NH2:47])=[O:46].C(O)(C)C>N1C=CC=CC=1.CN(C=O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][C:19]3([C:25](=[O:26])[NH:52][C:51]4[CH:50]=[CH:49][CH:48]=[C:44]([C:45](=[O:46])[NH2:47])[C:43]=4[NH2:42])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 27560931-((Fmoc)amino)cyclohexanecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 534228072,3-Diaminobenzamide dihydrochloride

Produkt 1

HCID 68508528[1-(2-Amino-3-carbamoyl-phenylcarbamoyl)-cyclohexyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 1-(9H-fluoren-9-ylmethoxycarbonyl amino)-cyclohexanecarboxylic acid (0.326 g, 0.9 mmol) in pyridine (1 mL) and DMF (1 ml) was heated to 40° C. for 30 min. Carbonyl diimidazole (0.15 g, 0.9 mmol) was added and the mixture was stirred at 40° C. for 1 hour then treated with 2,3-diamino-benzamide dihydrochloride (prepared as described in WO0026192, 0.2 g, 0.9 mmol). After stirring for 1 hour at room temperature, isopropyl alcohol (3 ml) was added and the solution was cooled overnight at 0° C. The precipitated solid was filtered, dissolved in water (3 ml), treated with 50% aqueous NaOH (0.071 ml) then stirred for 3 hours at room temperature. The mixture was filtered and used immediately in Example 48B.

Aufarbeitung

  1. stirringAfter stirring for 1 hour at room temperature
  2. temperaturethe solution was cooled overnight at 0° C
  3. filtrationThe precipitated solid was filtered
  4. dissolutiondissolved in water (3 ml)
  5. additiontreated with 50% aqueous NaOH (0.071 ml)
  6. stirringthen stirred for 3 hours at room temperature
  7. filtrationThe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-3c7f730b94f942349c7865919bff10b4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728026B2

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