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Sodium cyanoborohydride → 1-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-(2-(3,5-dimethylphenyl)-3-{2-[(4-pyridin-4-yl-butyl)-(2-pyridin-3-yl-ethyl)amino]ethyl}-1H-indol-5-yl)-2-methylpropan-1-one

HRID 1274396
ノート
印刷プレビュー

反応式

HRID 1274396 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH:10]=O)=[CH:3][CH:2]=1.[CH:12]12[N:18]([C:19](=[O:51])[C:20]([C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][C:27]([C:32]3[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=3)=[C:26]4[CH2:40][CH2:41][NH:42][CH2:43][CH2:44][C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)([CH3:22])[CH3:21])[CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH:15]12[N:18]([C:19](=[O:51])[C:20]([C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][C:27]([C:32]3[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=3)=[C:26]4[CH2:40][CH2:41][N:42]([CH2:10][CH2:9][CH2:8][CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:43][CH2:44][C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)([CH3:21])[CH3:22])[CH:12]([CH2:13][CH2:14]1)[CH2:17][CH2:16]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 114464344-Pyridin-4-ylbutanalHCID 221206711-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-{2-(3,5-dimethylphenyl)-3-[2-(2-pyridin-3-yl-ethylamino)-ethyl]-1H-indol-5-yl)-2-methylpropan-1-one

生成物 1

HCID 221206761-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-(2-(3,5-dimethylphenyl)-3-{2-[(4-pyridin-4-yl-butyl)-(2-pyridin-3-yl-ethyl)amino]ethyl}-1H-indol-5-yl)-2-methylpropan-1-one収率 75.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 4-(pyridin-4-yl)butyraldehyde (29 mg in 1.5 mL dry methanol) was added 18 mg of 1-(7-aza-bicyclo[2.2.1]hept-7-yl)-2-(2-(3,5-dimethylphenyl)-3-[2-(2-pyridin-3-yl-ethylamino)-ethyl]-1H-indol-5-yl}-2-methylpropan-1-one followed by 10 mg 3A powdered molecular seives. To this mixture, 13 mg sodium cyanoborohydride was added and the pH adjusted to 5.5 by the addition of 10% methanolic acetic acid. After 17.5 hours, the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion was 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 (methylene chloride:methanol, 90:10) gave the title compound (17 mg).

後処理

  1. customthe reaction was quenched by the addition of saturated sodium bicarbonate
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic portion was 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 (methylene chloride:methanol, 90:10)

出典と根拠

ORDレコード
ord-6fdfb094099b4ee889d142c30c6c9f9a
出典データセット
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06156767

反応ノート

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