1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-Fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide

HRID 855441

Reaction equation

HRID 855441 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:34]=[CH:33][C:21]([CH2:22][NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[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:34]=[CH:33][C:21]([CH2:22][N:23]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[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 116939945-fluoro-1H-indole-7-carboxylic acidHCID 29280418(4-Tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amine

Product 1

HCID 866031245-Fluoro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amideYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

66 mg (0.33 mol) of 5-fluoro-1H-indol-7-carboxylic acid, 86 mg (0.30 mmol) of (4-tert-butyl-benzyl)-[2-(4-fluoro-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 98 mg (73%) product as a light yellow viscous oil. MS (ISP) 447.2 (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-f4b8a8ae2fb1426aa72070bd643355cc
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Linked notes

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