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 1421538Notes

Reaction equation

HRID 1421538 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 tic 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 tic on silica gel

Sources & evidence

ORD record
ord-c00f5754b97645f9a61bd8fc01ac0153
Source dataset
uspto-grants-2000_06
Patent number
US06077858

Reaction notes

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