1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-Fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amide

HRID 855445Notes

Reaction equation

HRID 855445 reaction equation
[F:1][C:2]1[C:10]([C:11]([OH:13])=O)=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:14]([C:18]1[CH:35]=[CH:34][C:21]([CH2:22][NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CCN=C=NCCCN(C)C.Cl>ClCCCl>[C:14]([C:18]1[CH:35]=[CH:34][C:21]([CH2:22][N:23]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:11]([C:10]2[C:2]([F:1])=[CH:3][CH:4]=[C:5]3[C:9]=2[NH:8][CH:7]=[CH:6]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 117081616-fluoro-1H-indole-7-carboxylic AcidHCID 68563688(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine

Product 1

HCID 866031276-Fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amideYield 43.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

98 mg (0.55 mol) of 6-fluoro-1H-indol-7-carboxylic acid, 168 mg (0.50 mmol) of (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine and 105 mg (0.55 mmol) of EDC.HCl were dissolved in 5 ml 1,2-dichloro-ethane. The reaction mixture was stirred at rt over night and heated to 80° C. for 3 h. The solvent was evaporated and the residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 4:1) to yield 108 mg (43%) product as a colorless viscous oil. MS (ISP) 497.2 (M+H)+.

Workup

  1. temperatureheated to 80° C. for 3 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-edaa4b4bf823469abebd5c0b52f0c868
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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