1,2-Dichloroethane → (4-Cyclobutylhexahydro-1H-1,4-diazepin-1-yl)[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone

HRID 2261223Notes

Reaction equation

HRID 2261223 reaction equation
[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

Participants

8

Reactant 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

Product 1

HCID 66930417(4-Cyclobutylhexahydro-1H-1,4-diazepin-1-yl)[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanoneYield 43.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-bb53c593a28f4463b0096302bb7243e4
Source dataset
uspto-grants-2010_12
Patent number
US07846922B2

Reaction notes

Loading…