Acetic Acid → HCID 9940142, compound

HRID 1274258Notes

Reaction equation

HRID 1274258 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].[CH:19]([N:22]([CH:45]([CH3:47])[CH3:46])[C:23]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1)=[C:28]2[CH2:42][CH2:43][NH2:44])=[O:24])([CH3:21])[CH3:20].[C:48]([BH3-])#[N:49].[Na+]>CO>[CH:45]([N:22]([CH:19]([CH3:21])[CH3:20])[C:23]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:34]1[CH:35]=[C:36]([CH3:41])[CH:37]=[C:38]([CH3:40])[CH:39]=1)=[C:28]2[CH2:42][CH2:43][N:44]([CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:3]2[CH:2]=[N:49][CH:48]=[CH:15][CH:16]=2)=[CH:8][CH:9]=1)[CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:8][CH:9]=1)=[O:24])([CH3:47])[CH3:46]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 542715753-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisopropylamide

Product 1

HCID 9940142HCID 9940142, compound

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 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisopropylamide 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.

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-96b9e1f2208846a0937fa2dd873e42a9
Source dataset
uspto-grants-2000_12
Patent number
US06156772

Reaction notes

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