1,2-Dichloroethane → tert-butyl[(6-{[(2,2,2-trifluoroethyl)amino]carbonyl}-3H-imidazo[4,5-b]pyridin-2-yl)methyl]carbamate

HRID 908249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908249
CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[NH:40][C:32]2=[N:33][CH:34]=[C:35]([C:37]([OH:39])=O)[CH:36]=[C:31]2[N:30]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C1C=CC2N(O)N=NC=2C=1.[F:51][C:52]([F:56])([F:55])[CH2:53][NH2:54].CCN(C(C)C)C(C)C.C(Cl)CCl>>[C:20]([O:24][C:25](=[O:26])[NH:27][CH2:28][C:29]1[NH:40][C:32]2=[N:33][CH:34]=[C:35]([C:37]([NH:54][CH2:53][C:52]([F:56])([F:55])[F:51])=[O:39])[CH:36]=[C:31]2[N:30]=1)([CH3:21])([CH3:22])[CH3:23]

Komponenten

7

Edukt 6

HCID 111,2-DichloroethaneHCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178453117HCID 178453117, Verbindung

Produkt 1

HCID 178453116tert-butyl[(6-{[(2,2,2-trifluoroethyl)amino]carbonyl}-3H-imidazo[4,5-b]pyridin-2-yl)methyl]carbamateAusbeute 70 %

Versuchsvorschrift

To a DMF 3 mL solution of 2-{[(tert-butoxycarbonyl)amino]methyl}-3H-imidazo[4,5-b]pyridine-6-carboxylic acid (293 mg, 1.0 mmol) were added HOBt (162 mg, 1.2 mmol), 2,2,2-trifluoroethanamine (130 mg, 1.5 mmol), DIPEA (388 mg, 3.0 mmol) and EDC (288 mg, 1.5 mmol). The reaction mixture was stirred at room temperature overnight and was partitioned between EtOAc and water. The organic layer was washed with brine twice, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by prep TLC (MeOH/CH2Cl2=1/10, v/v) to give the title compound (0.26 g, 70%).

Aufarbeitung

  1. customwas partitioned between EtOAc and water
  2. washThe organic layer was washed with brine twice
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep TLC (MeOH/CH2Cl2=1/10

Quellen und Nachweise

ORD-Eintrag
ord-872af5c2ca894d9689025acd060e1929
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017605B2

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