Triethylamine → [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone

HRID 1913150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913150
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)[CH2:15][CH2:14]1.Cl.C(N=C=N)C.C(N(CC)CC)C>ClC(Cl)C.CN(C)C1C=CN=CC=1>[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[CH:16]1[CH2:17][CH2:18][N:13]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:10])[CH2:14][CH2:15]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 21883477Ethylcarbodiimide hydrochlorideHCID 450738062-(piperidin-4-yl)-1H-benzimidazole dihydrochloride

Produkt 1

HCID 58494556[4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanoneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 5-bromopyridine-2-carboxylic acid (177 mg, 0.88 mmol) and 2-(piperidin-4-yl)-1H-benzimidazole dihydrochloride (200 mg, 0.73 mmol) in dichloroethane (5 mL) is added ethylcarbodiimide hydrochloride (168 mg, 0.88 mmol), triethylamine (0.25 mL, 1.82 mmol) and 4-dimethylaminopyridine (44.6 mg, 0.36 mmol). After 3 h the reaction mixture is washed with saturated aqueous NaHCO3, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration from hot EtOAc gives 39.4 mg of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](5-bromopyridin-2-yl)methanone.

Aufarbeitung

  1. washAfter 3 h the reaction mixture is washed with saturated aqueous NaHCO3, water and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2f0ceccfa4b24f44ad7d7b34e5f88c48
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609696B2

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