Water → N-[2-(3-amidinophenoxy)ethyl]-4-trifluoromethylbenzamide trifluoroacetate

HRID 747672Notes

Reaction equation

HRID 747672 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C([N:16](CC)CC)C.Cl.CN(C)CCCN=C=NCC.[OH:33]N1C2C=CC=CC=2N=N1.Cl.[NH2:44][CH2:45][CH2:46][O:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][CH:55]=1)[C:51]#[N:52].[OH2:56]>ClCCl>[F:1][C:2]([F:13])([F:12])[C:3]([OH:33])=[O:56].[C:51]([C:50]1[CH:49]=[C:48]([CH:55]=[CH:54][CH:53]=1)[O:47][CH2:46][CH2:45][NH:44][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=1)(=[NH:16])[NH2:52]

Participants

8

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 99664-(Trifluoromethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226451983-(2-Aminoethoxy)benzonitrile hydrochloride

Product 1

HCID 17788865N-[2-(3-amidinophenoxy)ethyl]-4-trifluoromethylbenzamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

194 mg (1.02 mmol) of 4-trifluoromethylbenzoic acid was dissolved in 10 ml of dichloromethane. 0.43 ml (3.06 mmol) of triethylamine, 215 mg (1.12 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 152 mg (1.12 mmol) of 1-hydroxybenzotriazole and 203 mg (1.02 mmol) of 3-(2-aminoethoxy)benzonitrile hydrochloride were added to the solution, and they were stirred for 20 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was treated in the same manner as that of step 6 in Example 1 to obtain the title compound.

Workup

  1. customThe reaction liquid
  2. extractionAfter the extraction with ethyl acetate
  3. washthe organic layer was washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. additionthe residue was treated in the same manner as that of step 6 in Example 1

Sources & evidence

ORD record
ord-5a49473140d540eab95c5cd1640e039e
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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