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Triethylamine → 5-(1-(4-Cyanobenzyl)-5-imidazolylmethyl)-4,5,6,7-tetrahydrothieno[3,2-]pyridine

HRID 850027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 850027
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11]([C:13]1[CH:26]=[CH:25][C:16]([CH2:17][N:18]2[C:22]([CH:23]=O)=[CH:21][N:20]=[CH:19]2)=[CH:15][CH:14]=1)#[N:12].C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(C(Cl)Cl)(Cl)Cl.CCOC(C)=O>[C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[C:22]([CH2:23][CH:9]3[CH2:10][C:5]4[CH:4]=[CH:3][S:2][C:6]=4[NH:7][CH2:8]3)=[CH:21][N:20]=[CH:19]2)=[CH:25][CH:26]=1)#[N:12]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chlorideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Produkt 1

HCID 867550765-(1-(4-Cyanobenzyl)-5-imidazolylmethyl)-4,5,6,7-tetrahydrothieno[3,2-]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 65911,1,2,2-TetrachloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (Halczenko and Hartman; Synthetic Commun., 1996, 26, 1363; 0.439 g, 2.5 mmol) in CHCl2CHCl2 (15 mL) was added 1-(4-cyanobenzyl)-5-imidazole carboxaldehyde (0.58 g, 2.75 mmol), 4 Å sieves and triethylamine (0.35 mL, 2.5 mmol) followed by NaBH(OAc)3 (1.59 g, 7.5 mmol). The mixture was stirred at room temperature for 16 h., the mixture was diluted with EtOAc, filtered through celite, washed with brine, dried (Na2SO4) and concentrated. The residue was stirred in 2N HCl (50 mL) for 2 h. then extracted with ether. The aqueous layer was basified with 40% NaOH solution and extracted 3× CH2Cl2 which was then washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. Chromatography (silica gel; 2.5% MeOH in CHCl3) followed by crystallization from ether afforded the title compound as a white solid.

Aufarbeitung

  1. filtrationfiltered through celite
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. stirringThe residue was stirred in 2N HCl (50 mL) for 2 h.
  6. extractionthen extracted with ether
  7. extractionextracted 3× CH2Cl2 which
  8. washwas then washed with brine
  9. dry with materialdried (Na2SO4)
  10. customthe solvent evaporated in vacuo
  11. customChromatography (silica gel; 2.5% MeOH in CHCl3) followed by crystallization from ether

Quellen und Nachweise

ORD-Eintrag
ord-3396347695614d22be0f30b5f8dc4b87
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06015817

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