Cesium carbonate → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-6-{[2-(propylamino)ethyl]amino}-1,2-benzisothiazole-3-carboxamide

HRID 2362858노트

반응식

HRID 2362858 반응식
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P([C:41]2[CH:46]=[CH:45]C=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65](Br)=[CH:66][C:61]=3[S:60][N:59]=1)=[O:57])[CH2:48]2.C(=O)([O-])[O-].[Cs+].[Cs+].N1CCCC1=O.C[N:81]1[CH2:85][CH2:84][NH:83]C1=O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65]([NH:81][CH2:85][CH2:84][NH:83][CH2:45][CH2:46][CH3:41])=[CH:66][C:61]=3[S:60][N:59]=1)=[O:57])[CH2:48]2

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10044409HCID 10044409, 화합물HCID 672293681-Methyl-2-imidazolidinone 2-pyrrolidinone

생성물 1

HCID 67230658N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-6-{[2-(propylamino)ethyl]amino}-1,2-benzisothiazole-3-carboxamide수율 70%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

Palladium (II) acetate (0.09 mmol) was added to a solution of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.14 mmol) in toluene (8 mL) and the reaction mixture was maintained until the contents completely dissolved. The resultant yellow solution was transferred to a mixture of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1,2-benzisothiazole-3-carboxamide (0.33 mmol), cesium carbonate (0.39 mmol) and 1-methyl-2-imidazolidinone 2-pyrrolidinone (0.500 mmol) under an atmosphere of nitrogen gas and the reaction mixture was heated at 100° C. for 16 h. The reaction mixture was filtered through Celite and concentrated. The residue was purified by HPLC, thus providing the product in 70% yield.

후처리

  1. temperaturethe reaction mixture was maintained until the contents
  2. dissolutioncompletely dissolved
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC
  6. customthus providing the product in 70% yield

출처 및 근거

ORD 기록
ord-cee1c0458c464293ac21f821f08e6064
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691841B2

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