Triethylamine → HCID 178424284, Verbindung

HRID 1979321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979321
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:11]=[C:12]([C:16]2[NH:20][N:19]=[N:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.[C:33]1([CH3:61])[C:34]([C:39]([CH2:41][N:42]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[N:46]([C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:45][CH:44]([NH2:59])[C:43]2=[O:60])=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[C:33]1([CH3:61])[C:34]([C:39]([CH2:41][N:42]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[N:46]([C:53](=[O:58])[C:54]([CH3:56])([CH3:57])[CH3:55])[CH2:45][CH:44]([NH:59][C:22]([NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]4[NH:20][N:19]=[N:18][N:17]=4)[CH:11]=3)=[O:24])[C:43]2=[O:60])=[O:40])=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

8

Edukt 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 212016481-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 212019913-(2H-tetrazol-5-yl)-phenylamine hydrochloride

Produkt 1

HCID 178424284HCID 178424284, VerbindungAusbeute 144,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triethylamine (0.44 ml) was added to a suspension of 5-(3-aminophenyl)tetrazole hydrochloride (prepared according to International Publication WO93/17011) (316 mg) in anhydrous tetrahydrofuran (10 ml). After cooled at 0° C., triphosgene (157 mg) was added, and the mixture was adjusted to pH 8 with triethylamine (0.22 ml). After returned at room temperature, stirred for 30 minutes, 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (472 mg) obtained from Step 3 of Example 1 in anhydrous tetrahydrofuran (10 ml) was added to the reaction mixture, and then stirred at room temperature for one hour. Ethyl acetate (20 ml) was added to the resultant mixture, 10% acetic acid (20 ml) was added thereto and separated into organic layer and aqueous layer. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=5:1) and the mixed solvent of isopropyl ether and ethanol was added to the residue for trituration, collected by filtration, to thereby obtain 443 mg of the title compound (Yield: 63.6%) as white powder.

Aufarbeitung

  1. customAfter returned at room temperature
  2. stirringstirred at room temperature for one hour
  3. additionwas added
  4. customseparated into organic layer and aqueous layer
  5. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)
  8. additionthe mixed solvent of isopropyl ether and ethanol was added to the residue for trituration
  9. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e84f9def7b684e72b5be87ee5be9a19c
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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