1H-Indole-7-carboxylic acid → HCID 69347324, compound

HRID 855434Notes

Reaction equation

HRID 855434 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[C:31](O)=[O:32])[CH:24]=[CH:23]1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][CH:16]=1)[C:31]([C:29]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:30]=1[NH:22][CH:23]=[CH:24]2)=[O:32])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69347213HCID 69347213, compound

Product 1

HCID 69347324HCID 69347324, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.37 g (15 mmol) of 3-(4-tert-butyl-benzylamino)-propionic acid tert-butyl ester, 2.42 g (15 mmol) of 1H-indole-7-carboxylic acid and 3.25 g (16.5 mmol) of EDC.HCl were dissolved in 50 ml DCM. The reaction mixture was stirred at rt over night, washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave 6.25 g (97%) product as a white solid. MS (ISP) 435.4 (M+H)+.

Workup

  1. washwashed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-87a5ad3d8eb746a1af1c0932a9e25ec3
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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