1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86603119, compound

HRID 855436Notes

Reaction equation

HRID 855436 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:14]([C:18]1[CH:36]=[CH:35][C:21]([CH2:22][NH:23][CH2:24][CH2:25][N:26]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[CH3:27])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:14]([C:18]1[CH:36]=[CH:35][C:21]([CH2:22][N:23]([CH2:24][CH2:25][N:26]([C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[CH3:27])[C:11]([C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[CH:5]3)=[O:13])=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668685635-chloro-1H-indole-7-carboxylic acidHCID 68578813N1-(4-Chlorophenyl)-N2-[[4-(1,1-dimethylethyl)phenyl]methyl]-N1-methyl-1,2-ethanediamine

Product 1

HCID 86603119HCID 86603119, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

98 mg (0.50 mol) of 5-chloro-1H-indole-7-carboxylic acid, 165 mg (0.5 mmol) of N′-(4-tert-butyl-benzyl)-N-(4-chloro-phenyl)-N-methyl-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) 508.4 (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-419fbd0dc52a4d59aaf6a42dcf7e3d4a
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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