Tris(hydroxymethyl)aminomethane → HCID 178461736, Verbindung

HRID 1158754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158754
[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C@@H:15]([NH2:17])[CH3:16])[C:6]=2[N:18]=1.C1CCC([N:28]=[C:29]=[N:30]C2CCCCC2)CC1.C(OC(NC(NC(OC(C)(C)C)=O)=S)=O)(C)(C)C.C(O)C(N)(CO)CO>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C@@H:15]([NH:17][C:29]([NH2:30])=[NH:28])[CH3:16])[C:6]=2[N:18]=1

Komponenten

6

Edukt 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 10868DicyclohexylcarbodiimideHCID 5193990N,N'-Di-Boc-thioureaHCID 595136442-amino-9-[(2S)-2-aminopropyl]-9H-pyrido[2,3-b]indole-3-carboxamide

Produkt 1

HCID 178461736HCID 178461736, VerbindungAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-9-[(2S)-2-aminopropyl]-9H-pyrido[2,3-b]indole-3-carboxamide (30, 100 mg, 0.350 mmol) in methylene chloride (3 mL) was added PL-DCC resin (394 mg, 0.575 mmol) and the mixture was stirred at room temperature for 15 min. N,N′-bis-tert-butoxycarbonylthiourea (112 mg, 0.406 mmol) was added and the reaction mixture was stirred at room temperature overnight. PS-trisamine resin (4.12 g, 3.6 mmol/g, 14.8 mmol) was subsequently added and the resulting mixture was stirred at room temperature overnight. The resins were removed by suction filtration and the filtrate was concentrated under reduced pressure. Purification of the crude material by reverse phase C-18 silica gel chromatography [0-70% acetonitrile in water (containing 0.1% TFA)] afforded 2-amino-9-((2S)-2-{[amino(imino)methyl]amino}propyl)-9H-pyrido[2,3-b]indole-3-carboxamide (71, 48 mg 26%). NH4OAc standard conditions. DAD Retention time =4.98 min. M+H=326.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customThe resins were removed by suction filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification of the crude material by reverse phase

Quellen und Nachweise

ORD-Eintrag
ord-750d344f00054e08a1c8a4a4607747bb
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812018B2

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