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

HRID 1274388Notes

Reaction equation

HRID 1274388 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]=O)[CH:2]=1.[NH2:10][CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([CH3:33])([CH3:32])[C:23]([N:25]3[CH:29]4[CH2:30][CH2:31][CH:26]3[CH2:27][CH2:28]4)=[O:24])[CH:20]=2)[NH:15][C:14]=1[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1.[C:42]([BH3-])#[N:43].[Na+]>CO.C(O)(=O)C>[CH:26]12[N:25]([C:23](=[O:24])[C:22]([C:19]3[CH:20]=[C:21]4[C:16](=[CH:17][CH:18]=3)[NH:15][C:14]([C:34]3[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=3)=[C:13]4[CH2:12][CH2:11][N:10]([CH2:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8][CH2:7][C:3]3[CH:2]=[N:43][CH:42]=[CH:5][CH:4]=3)([CH3:33])[CH3:32])[CH:29]([CH2:28][CH2:27]1)[CH2:30][CH2:31]2

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 11073404Pyridin-3-ylacetaldehydeHCID 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

Product 1

HCID 99174031-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-[3-{2-[bis-(2-pyridin-3-yl-ethyl)-amino]ethyl}-2-(3,5-dimethyl-phenyl)-1H-indol-5-yl]-2-methylpropan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

To a solution of pyridin-3-yl-acetaldehyde (120 mg in a mixture of 5 mL methanol and 0.018 mL glacial acetic acid) was added 141 mg of 2-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-aza-bicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one followed by 20 mg 3Å powdered molecular seives. To this mixture, 68 mg sodium cyanoborohydride was added and the pH adjusted to 5.5 by the addition of 10% methanolic acetic acid. After 15.5 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, 92:8) gave the title compound (130 mg). MASS: 640 (M+H)

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, 92:8)

Sources & evidence

ORD record
ord-1268b9d86c5244aa9d6ce97156807bae
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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