Hydrochloric Acid → 2,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-8-amino-1H-1,4-benzodiazepine, dihydrochloride

HRID 849389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 849389
[ClH:1].Cl.[NH:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=[CH:19][C:14]=3[CH2:13][N:12]([C:23]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[O:24])[CH2:11][CH2:10]2)[N:5]=[CH:4]1.[OH-].[Na+].C([O-])(O)=O.[Na+].Cl.Cl.Cl.N1C=C(CN2C3C=C(NC(=O)C)C=CC=3CN(C(C3C4C(=CC=CC=4)C=CC=3)=O)CC2)N=C1>CC(O)=O.O.CCOCC>[ClH:1].[ClH:1].[NH:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:14]=3[CH2:13][N:12]([C:23]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[O:24])[CH2:11][CH2:10]2)[N:5]=[CH:4]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 178474025N-[2,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepin-8-yl]acetamide, dihydrochlorideHCID 1784788782,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-8-nitro-1H-1,4-benzodiazepine, dihydrochloride

Produkt 1

HCID 1784786502,3,4,5-Tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-8-amino-1H-1,4-benzodiazepine, dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

16% aqueous TiCl3 (2 mL) was added to a solution of Example 25 (0.10 g, 0.23 mmol) in AcOH/H2O (2 mL, 1:1). After stirring for 15 min, the reaction was made basic with 1N NaOH and NaHCO3 and stirred for 30 min. The layers were separated and the aqueous layer was reextracted with CHCl3 /CH3OH (9/1). The combined organic layers were dried over MgSO4, filtered and concentrated to afford 0.92 g. (73%) of Example 26. A 20 mg. sample of this material was treated with 1M HCl in ether (2 mL). A light yellow solid was formed which was triturated several times with ether and dried under vacuum to afford Example 26 (23 mg.) as a light yellow solid. (Example 26 is also Compound G of Example 22.)

Aufarbeitung

  1. stirringstirred for 30 min
  2. customThe layers were separated
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 0.92 g
  7. customA light yellow solid was formed which
  8. customwas triturated several times with ether
  9. customdried under vacuum
  10. customto afford Example 26 (23 mg.) as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-39c59d78eb3e475e801df6ae0e82f595
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011029

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