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Trifluoroacetic acid → 2-(3,5-dimethylphenyl)-3-[2-(1-methyl-4-pyridin-3-yl-butylamino)ethyl]-1H-indole-5-carboxylic acid diisobutylamide

HRID 1458362
Notes
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Reaction equation

HRID 1458362 reaction equation
[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[CH2:25][CH2:26][NH2:27])=[O:7])[CH:2]([CH3:4])[CH3:3].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][CH2:39][CH2:40][C:41](=O)[CH3:42])[CH:33]=1.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:11]2[CH2:25][CH2:26][NH:27][CH:41]([CH3:42])[CH2:40][CH2:39][CH2:38][C:34]1[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acid2×HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 137397405-(3-Pyridinyl)-2-pentanoneHCID 537946513-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide

Product 1

HCID 67664720
2-(3,5-dimethylphenyl)-3-[2-(1-methyl-4-pyridin-3-yl-butylamino)ethyl]-1H-indole-5-carboxylic acid diisobutylamide
Yield 48.5%

Procedure

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide (142 mg in dry methanol) was added 19 mg 5-pyridin-3-yl-pentan-2-one and the pH adjusted to 6 by the addition of trifluoroacetic acid. To this, approximately 10 mg of 3 Å molecular sieves were added followed by 27 mg of sodium cyanoborohydride. The pH was adjusted occasionally with trifluoroacetic acid over 36 hours to maintain pH of 6. The reaction was then quencehed by the addition of aqueous potassium carbonate and the mixture extracted with ethyl acetate. The organic portion was washed sequentially with aqueous potassium carbonate and brine, then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1) gave the title compound (32 mg) [m/e =567 (M+H)] plus unreacted amine (115 mg).

Workup

  1. additionTo this, approximately 10 mg of 3 Å molecular sieves were added
  2. temperatureto maintain pH of 6
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic portion was washed sequentially with aqueous potassium carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1)

Sources & evidence

ORD record
ord-b17f16c81c9f4a138f6f2a0fde11c7b8
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05849764

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes