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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
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Reaktionsgleichung

Reaktionsgleichung von HRID 1274396
[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
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Komponenten

5

Edukt 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

Produkt 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
Ausbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6fdfb094099b4ee889d142c30c6c9f9a
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06156767

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