(2-(4-Fluorophenyl)ethyl)(methyl)amine → 5-Bromo-thiophene-3-carboxylic acid [2-(4-fluorophenyl)-ethyl]-amide

HRID 1351321Notes

Reaction equation

HRID 1351321 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19]C)=[CH:13][CH:12]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][C:7]([C:4]2[CH:3]=[C:2]([Br:1])[S:6][CH:5]=2)=[O:9])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 120234(2-(4-Fluorophenyl)ethyl)(methyl)amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 434244315-Bromo-thiophene-3-carboxylic acid [2-(4-fluorophenyl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-thiophene-3-carboxylic acid (5 g) and [2-(4-fluorophenyl)-ethyl]methyl-amine (the compound of Preparation Example 14) (3.7 g) in dichloromethane (150 mL) was added 1-Ethyl-3-(3-dimethylamino propyl)-carbodiimide.hydrochloride (5.1 g) was added. After stirring for 1.5 hours, the residue resulting from evaporation of the reaction solution in vacuo was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (6 g) was obtained as a colorless oily matter.

Workup

  1. additionwas added
  2. customthe residue resulting from evaporation of the reaction solution in vacuo
  3. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-40a188d8ba934545bdb57b3afa5a4d09
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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