1H-Indole-7-carboxylic acid → 1H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(ethyl-m-tolyl-amino)-ethyl]-amide

HRID 855437Notes

Reaction equation

HRID 855437 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.[C:13]([C:17]1[CH:36]=[CH:35][C:20]([CH2:21][NH:22][CH2:23][CH2:24][N:25]([CH2:33][CH3:34])[C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:13]([C:17]1[CH:36]=[CH:35][C:20]([CH2:21][N:22]([CH2:23][CH2:24][N:25]([CH2:33][CH3:34])[C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)[C:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)=[O:12])=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:16]

Participants

5

Reactant 3

HCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69342865N'-(4-tert-butyl-benzyl)-N-ethyl-N-m-tolyl-ethane-1,2-diamine

Product 1

HCID 866031201H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(ethyl-m-tolyl-amino)-ethyl]-amideYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

81 mg (0.50 mol) of 1H-indole-7-carboxylic acid, 162 mg (0.5 mmol) of N′-(4-tert-butyl-benzyl)-N-ethyl-N-m-tolyl-ethane-1,2-diamine and 108 mg (0.55 mmol) of EDC.HCl were dissolved in 5 ml DCM. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was dissolved in diethyl ether. The organic layer was washed with 1N aqueous HCl solution, once with 1N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave 140 mg (55%) product as a colorless oil. MS (ISP) 468.4 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in diethyl ether
  3. washThe organic layer was washed with 1N aqueous HCl solution, once with 1N aqueous NaOH solution and once with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-39ee5e229e144f9586dff008529c1e34
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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