1,2-Dichloroethane → 1-cyclobutyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}hexahydro-1H-1,4-diazepine

HRID 452867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452867
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[CH:35]1([N:39]2[CH2:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1>CN(C=O)C.O.C(N(CC)CC)C>[CH:35]1([N:39]2[CH2:45][CH2:44][CH2:43][N:42]([C:13]([C:12]3[CH:11]=[CH:10][C:9]([B:4]4[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]4)=[CH:17][CH:16]=3)=[O:15])[CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 574239521-Cyclobutyl-1,4-diazepane dihydrochloride

Produkt 1

HCID 669304171-cyclobutyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}hexahydro-1H-1,4-diazepineAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.24 g) in dry DMF (30 ml) was treated with EDC (1.48 g) and HOBT (0.67 g). The reaction mixture was stirred at rt for 5 min, followed by the addition of 1-(cyclobutyl)hexahydro-1H-1,4-diazepine dihydrochloride (D4) (1.13 g) and triethylamine (2.7 ml). The mixture was stirred at rt overnight. The reaction mixture was then poured into water (250 ml) and extracted with EtOAc (2×35 ml). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2×30 ml) followed by water (5×30 ml). After drying (magnesium sulphate) the solution was evaporated to give the title compound (D7) as an oil (0.84 g). MS electrospray (+ve ion) 385 (MH+).

Aufarbeitung

  1. stirringThe mixture was stirred at rt overnight
  2. extractionextracted with EtOAc (2×35 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2×30 ml)
  4. dry with materialAfter drying (magnesium sulphate) the solution
  5. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-dc33f5737faf40c7b1c2a22cbf9f7e76
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492375B2

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