1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69513555, compound

HRID 855444Notes

Reaction equation

HRID 855444 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:34]=[CH:33][C:21]([CH2:22][NH:23][CH2:24][CH2:25][CH:26]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)[CH3:27])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].[CH3:35]CN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:14]([C:18]1[CH:34]=[CH:33][C:21]([CH2:22][N:23]([CH2:24][CH2:25][CH:26]([C:28]2[O:29][C:30]([CH3:35])=[CH:31][CH:32]=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)([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668685635-chloro-1H-indole-7-carboxylic acidHCID 69347760HCID 69347760, compound

Product 1

HCID 69513555HCID 69513555, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65 mg (0.33 mol) of 5-chloro-1H-indol-7-carboxylic acid, 89 mg (0.30 mmol) of [rac]-(4-tert-butyl-benzyl)-(3-furan-2-yl-butyl)-amine and 63 mg (0.33 mmol) of EDC.HCl were dissolved in 3 ml DCM. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was purified by column chromatography (20 g silica gel, heptane/EtOAc 4:1) to yield 94 mg (66%) product as a colorless viscous oil. MS (ISP) 477.2 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (20 g silica gel, heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-f72e3902ec364cd9a996935291107c0a
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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