1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-Fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide

HRID 855440Notes

Reaction equation

HRID 855440 reaction equation
[F: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:33]=[CH:32][C:21]([CH2:22][NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[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:33]=[CH:32][C:21]([CH2:22][N:23]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11]([C:9]2[CH:10]=[C:2]([F: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 4559933(4-Tert-butyl-benzyl)-phenethyl-amineHCID 116939945-fluoro-1H-indole-7-carboxylic acid

Product 1

HCID 866031235-Fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

66 mg (0.33 mol) of 5-fluoro-1H-indol-7-carboxylic acid, 80 mg (0.30 mmol) of (4-tert-butyl-benzyl)-2-phenyl-ethyl-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 7:3) to yield 85 mg (66%) product as a light yellow viscous oil. MS (ISP) 429.4 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-661b90f922194e17929b8d89502f845a
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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