1,2-Dichloroethane → HCID 68429731, 화합물

HRID 15485노트

반응식

HRID 15485 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 68429731HCID 68429731, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bd307917e22443d8b06f0c2696131e13
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732477B2

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