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Acetic Acid → 1-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-[3-{2-[bis-(4-pyridin-3-yl-benzyl)amino]-ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methyl-propan-1-one

HRID 1274248
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HRID 1274248 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:2]=1.[C:15](O)(=O)[CH3:16].[NH2:19][CH2:20][CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([CH3:42])([CH3:41])[C:32]([N:34]3[CH:38]4[CH2:39][CH2:40][CH:35]3[CH2:36][CH2:37]4)=[O:33])[CH:29]=2)[NH:24][C:23]=1[C:43]1[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=1.[C:51]([BH3-])#[N:52].[Na+]>CO>[CH:35]12[N:34]([C:32](=[O:33])[C:31]([C:28]3[CH:29]=[C:30]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([C:43]3[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=3)=[C:22]4[CH2:21][CH2:20][N:19]([CH2:11][C:10]3[CH:13]=[CH:14][C:7]([C:3]4[CH:2]=[N:52][CH:51]=[CH:15][CH:16]=4)=[CH:8][CH:9]=3)[CH2:11][C:10]3[CH:13]=[CH:14][C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[CH:8][CH:9]=3)([CH3:42])[CH3:41])[CH:38]([CH2:37][CH2:36]1)[CH2:39][CH2:40]2
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참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 117617912-[3-(2-Aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one

생성물 1

HCID 99185711-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-[3-{2-[bis-(4-pyridin-3-yl-benzyl)amino]-ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methyl-propan-1-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2.5 equivalents 4-pyridin-3-yl-benzaldehyde in a mixture of methanol and glacial acetic acid is added 2-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one followed by 3 Å powdered molecular seives. To this mixture, an excess of sodium cyanoborohydride is added and the pH adjusted to 5.5 by the addition of 10% methanolic acetic acid. After completion, the reaction is quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion is washed successively with saturated ammonium chloride, sodium bicarbonate and brine, then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel gives the title compound. MASS: 764 (M+H)

후처리

  1. customAfter completion, the reaction is quenched by the addition of saturated sodium bicarbonate
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic portion is washed successively with saturated ammonium chloride, sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-490a51c96e4e4aeaba2fe7ccc1f51ee1
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06156772

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