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 1274396Notes

Reaction equation

HRID 1274396 reaction equation
[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

Participants

5

Reactant 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

Product 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-oneYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6fdfb094099b4ee889d142c30c6c9f9a
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

Loading…