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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
Notes
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Reaction equation

HRID 1274248 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic Acid2×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

Product 1

HCID 9918571
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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-490a51c96e4e4aeaba2fe7ccc1f51ee1
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06156772

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes