Sodium Hydroxide → N-(1H-benzoimidazol-2-ylmethyl)-N'-pyrimidin-2-ylmethyl-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

HRID 899746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899746
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]=O.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:19]([CH:25]1[C:34]2[N:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:28][CH2:27][CH2:26]1)[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C1COCC1.Br.CC(O)=O>[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH2:18][N:19]([CH:25]1[C:34]2[N:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH2:28][CH2:27][CH2:26]1)[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 10126019N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamineHCID 13751953Pyrimidine-2-carbaldehyde

Produkt 1

HCID 10127385N-(1H-benzoimidazol-2-ylmethyl)-N'-pyrimidin-2-ylmethyl-N-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21893785Acetic Acid Mixture with Hydrobromic AcidLösungsmittel

Versuchsvorschrift

Using General Procedure B: To a solution of the crude aldehyde from above (332 mg) and N′-(1H-benzoimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (49 mg, 0.14 mmol) in THF (2 mL) was added NaBH(OAc)3 (89 mg, 0.42 mmol) and the mixture was stirred at room temperature for 1.5 h. The crude material was dissolved in saturated HBr/AcOH (2 mL) and stirred at room temperature for 5 minutes. The solution was made basic with 10 N NaOH(aq) and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (200:5:1 CH2Cl2/MeOH/NH4OH) afforded a yellow oil (44 mg).

Aufarbeitung

  1. stirringstirred at room temperature for 5 minutes
  2. extractionextracted with CH2Cl2 (3×15 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude material by column chromatography on silica gel (200:5:1 CH2Cl2/MeOH/NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-b686d0e23c39411481fbdafea9f52a46
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354934B2

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