Sulfuric acid magnesium salt (1:1) → 2-(3,5-Dimethylphenyl)-3-{2-[(5-pyridin-3-yl-thiophen-2-ylmethyl)amino]-ethyl}-1H-indole-5-carboxylic acid diisopropylamide

HRID 1602349Notes

Reaction equation

HRID 1602349 reaction equation
[CH:1]([N:4]([CH:27]([CH3:29])[CH3:28])[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1)=[C:10]2[CH2:24][CH2:25][NH2:26])=[O:6])([CH3:3])[CH3:2].S([O-])([O-])(=O)=O.[Mg+2].[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]2[S:46][C:45]([CH:47]=O)=[CH:44][CH:43]=2)[CH:37]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO.C(Cl)(Cl)Cl>[CH:27]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=1)=[C:10]2[CH2:24][CH2:25][NH:26][CH2:47][C:45]1[S:46][C:42]([C:38]2[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=2)=[CH:43][CH:44]=1)=[O:6])([CH3:29])[CH3:28]

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 108994275-(Pyridin-3-yl)thiophene-2-carbaldehydeHCID 542715753-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisopropylamide

Product 1

HCID 539084822-(3,5-Dimethylphenyl)-3-{2-[(5-pyridin-3-yl-thiophen-2-ylmethyl)amino]-ethyl}-1H-indole-5-carboxylic acid diisopropylamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisopropylamide in a mixture of dry chloroform and methanol at 0° C. is added magnesium sulfate followed by 5-pyridin-3-yl-thiophene-2-carbaldehyde and the mixture stirred at low temperature. After 40 minutes, acetic acid is added followed by a solution of sodium cyanoborohydride and the mixture allowed to warm to room temperature. After completion, the reaction is quenched by the addition of saturated aqueous sodium bicarbonate, extracted with methylene chloride and the combined organics washed sequentially with water and brine. Purification of the concentrate by preparative tlc on silica gel gives the title compound.

Workup

  1. customAfter completion, the reaction is quenched by the addition of saturated aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. washthe combined organics washed sequentially with water and brine
  4. customPurification of the
  5. concentrationconcentrate by preparative tlc on silica gel

Sources & evidence

ORD record
ord-9e40501f00694793bde66ad3373eb7d7
Source dataset
uspto-grants-1999_11
Patent number
US05981550

Reaction notes

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