1,2-Dichloroethane → HCID 68429731, compound

HRID 658218Notes

Reaction equation

HRID 658218 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][C:10]([C:13]([OH:15])=O)=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:16](Cl)[CH2:17][Cl:18].[CH:20]1[CH:21]=C[C:23]2[N:28](O)N=[N:26][C:24]=2[CH:25]=1.C(N(CC)CC)C>CN(C=O)C>[ClH:18].[N:28]12[CH2:17][CH2:16][CH:25]([CH2:20][CH2:21]1)[C@@H:24]([NH:26][C:13]([C:10]1[S:11][C:12]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[CH:9]=1)=[O:15])[CH2:23]2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 131624097-Nitrobenzo[b]thiophene-2-carboxylic acid

Product 1

HCID 68429731HCID 68429731, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g (8.96 mmol) of 7-nitro-1-benzothiophene-2-carboxylic acid and 1.78 g (8.96 mmol) of R-3-aminoquinuclidine dihydrochloride are initially charged in 25 ml of DMF. At 0° C., 2.06 g (10.75 mmol) of EDC, 1.45 g (10.75 mmol) of HOBt and 4.50 ml (32.26 mmol) of triethylamine are added to the solution. The mixture is stirred at RT for 18 h. The reaction is terminated by addition of a 10% strength aqueous sodium bicarbonate solution, and ethyl acetate is added. The resulting precipitate is filtered off with suction. The mother liquor is extracted twice with ethyl acetate. The organic phases are combined and concentrated. Both the precipitate and the concentrated mother liquor are purified by silica gel column chromatography (mobile phase: dichloromethane/methanol/25% ammonia 100:10:2). The product fractions are concentrated, dissolved in a mixture of methanol and 1N hydrochloric acid, then again concentrated and dried under high vacuum. The resulting solid is triturated with acetonitrile, filtered off with suction and dried at 50° C. under reduced pressure. 1.10 g (32.8% of theory) of the title compound are obtained.

Workup

  1. customThe reaction is terminated by addition of a 10% strength aqueous sodium bicarbonate solution, and ethyl acetate
  2. additionis added
  3. filtrationThe resulting precipitate is filtered off with suction
  4. extractionThe mother liquor is extracted twice with ethyl acetate
  5. concentrationconcentrated
  6. customBoth the precipitate and the concentrated mother liquor are purified by silica gel column chromatography (mobile phase: dichloromethane/methanol/25% ammonia 100:10:2)
  7. concentrationThe product fractions are concentrated
  8. dissolutiondissolved in a mixture of methanol and 1N hydrochloric acid
  9. concentrationagain concentrated
  10. customdried under high vacuum
  11. customThe resulting solid is triturated with acetonitrile
  12. filtrationfiltered off with suction
  13. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-adacca01c3274ae581663c8c5115fdb2
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

Loading…