Diisopropylethylamine → N-(4-Chloro-3-trifluoro methyl phenyl)-2-[4-(4-pyridinyloxy)phenyl amino]-acetamide

HRID 1453793Notes

Reaction equation

HRID 1453793 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:7]=1)=[O:4].[N:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][C:20]3[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=3)=[CH:29][CH:28]=2)=[CH:7][C:8]=1[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 23077292-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamideHCID 115645894-(Pyridin-4-yloxy)aniline

Product 1

HCID 11742948N-(4-Chloro-3-trifluoro methyl phenyl)-2-[4-(4-pyridinyloxy)phenyl amino]-acetamideYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 146.1 mg (0.54 mmol) of compound 9 in dimethylformamide (DMF) is given to a solution of 100 mg (0.54 mmol) of compound 2 and 0.1 ml (0.59 mmol) N-Ethyl-diisopropylamine in DMF. The reaction mixture is heated to 100° C. for 6 h, then evaporated and the residue is purified by preparative HPLC to yield 10.7 mg (5%) colourless solid.

Workup

  1. customevaporated
  2. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-ecb7bb25ad3c4f0993528ccbb154ecad
Source dataset
uspto-grants-2009_01
Patent number
US07476683B2

Reaction notes

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