Potassium Carbonate → HCID 178419006, Verbindung

HRID 1582262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582262
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH2:30])[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1.C(OC([NH:38][C:39](N1C=CC=N1)=[N:40]C(OC(C)(C)C)=O)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.[NH4+].[Cl-]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH:30][C:39]([NH2:40])=[NH:38])[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 21984983(1H-Benzimidazol-2-ylmethyl)-(2-Aminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Produkt 1

HCID 178419006HCID 178419006, VerbindungAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of (1H-Benzimidazol-2-ylmethyl)-(2-Aminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (see AMD9720) (50 mg, 0.125 mmol) in THF (5 mL) was added added N,N′-di-t-butoxycarbonyl-pyrazole-1-carboxamidine (60 mg, 0.187 mmol) and potassium carbonate (35 mg, 0.25 mmol) and the mixture stirred overnight. The reaction was diluted with aqueous NH4Cl (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were dried (Na2SO4), concentrated and purified by chromatography on silica gel (5% MeOH/CH2Cl2) to give the desired product as a pale foam (51 mg, 64%). 1H NMR (CDCl3) δ1.47 (s, 9H), 1.48 (s, 9H), 1.81 (m, 1H), 2.00 (m, 2H), 2.26 (m, 2H), 2.71-2.88 (m, 2H), 3.89-4.05 (m, 5H), 4.73 (dd, 1H, J=15.5, 5.1 Hz), 4.96 (dd, 1H, J=15.5, 5.7 Hz), 7.12 (m, 7H), 7.36-7.44 (m, 3H), 7.55 (br s, 1H (NH)), 8.55 (m, 1H (NH)), 8.66 (d, 1H, J=5.1 Hz).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel (5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-34acd8035871416cbc928d8f0e63a735
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734191B2

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