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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
ノート
印刷プレビュー

反応式

HRID 1274248 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic Acid2 回HCID 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

生成物 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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-490a51c96e4e4aeaba2fe7ccc1f51ee1
出典データセット
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06156772

反応ノート

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