Potassium Carbonate → HCID 178419006, Verbindung

HRID 1157866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157866
[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 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) δ 1.47 (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, H (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-af7088596da043a49edd1aabdd92cdef
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807694B2

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