3-Chloro-4-(2-diethylaminoethoxy)phenylamine → 3-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide

HRID 735080Notes

Reaction equation

HRID 735080 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14](Cl)=[O:15].[Cl:17][C:18]1[CH:31]=[C:30]([NH2:32])[CH:29]=[CH:28][C:19]=1[O:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25].ClCCl.CO.N>>[Cl:17][C:18]1[CH:31]=[C:30]([NH:32][C:14](=[O:15])[C:13]#[C:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=2[Cl:1])[CH:29]=[CH:28][C:19]=1[O:20][CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 21584172Ammonia methanol dichloromethaneHCID 86060673(2-Chloro-4-trifluoromethylphenyl)propynoic acid chloride

Product 1

HCID 578457753-(2-Chloro-4-trifluoromethylphenyl)propynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide

Procedure

Prepared analogously to Example 4.1.d. from (2-chloro-4-trifluoromethylphenyl)propynoic acid chloride and [2-(2-chloro-4-aminophenoxy)ethyl]diethylamine. Yield: 0.26 g (27.5% of theory); C22H21Cl2F3N2O2 (M=473.32); calc.: molecular ion peak (M+H)+: 473/475; found: molecular ion peak (M+H)+: 473/475; Rf value: 0.5 (silica gel, dichloromethane/methanol/ammonia (9:1:0.1)).

Workup

  1. customPrepared analogously to Example 4.1.d

Sources & evidence

ORD record
ord-6d4721fdf7c24690a5dd6a5249ed452c
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…