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

HRID 612754Notes

Reaction equation

HRID 612754 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:49]([BH3-])#[N:50].[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][N:26]([CH2:47][C:45]1[S:46][C:42]([C:38]2[CH:37]=[N:50][CH:49]=[CH:40][CH:39]=2)=[CH:43][CH:44]=1)[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 154585183-{2-[Bis-(5-pyridin-3-yl-thiophen-2-ylmethyl)amino]ethyl}-2-(3,5-dimethylphenyl)-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 2.5 equivalents of 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-f0372d9786a74f1cb2d65a490881607d
Source dataset
uspto-grants-1999_12
Patent number
US06004984

Reaction notes

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