1,2-Dichloroethane → N-[2-(2-Azabicyclo[2.2.2]oct-2-ylcarbonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]acetamide

HRID 8792Notes

Reaction equation

HRID 8792 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[N:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:12]=2)[O:7][C:6]=1[C:29](O)=[O:30])(=[O:3])[CH3:2].Cl.[CH:33]12[CH2:40][CH2:39][CH:36]([CH2:37][CH2:38]1)[CH2:35][NH:34]2.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:33]12[CH2:40][CH2:39][CH:36]([CH2:37][CH2:38]1)[CH2:35][N:34]2[C:29]([C:6]1[O:7][C:8]2=[N:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:12]=[C:13]2[C:5]=1[NH:4][C:1](=[O:3])[CH3:2])=[O:30]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 219848442-Azabicyclo[2.2.2]octane hydrochlorideHCID 219849113-(Acetylamino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo-[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 10053720N-[2-(2-Azabicyclo[2.2.2]oct-2-ylcarbonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.027 g (0.0568 mmol) of the product from Step A in CH2Cl2 (0.6 mL) was treated with 2-azabicyclo[2.2.2]octane hydrochloride (0.009 g; 0.0625 mmol), EDC (0.016 g; 0.0852 mmol), DMAP (0.007 g; 0.0568 mmol), and 1-methylmorpholine (19 μL; 0.170 mmol), then stirred at room temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 568.0 (M+1), 570.0 (M+3); Rt=4.68 min.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  2. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Sources & evidence

ORD record
ord-670afcfaaaf549ff9091b4ef1486c46e
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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