3-Chloro-4-(2-diethylaminoethoxy)phenylamine → 3-pyridin-2-ylpropynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

HRID 735082Notes

Reaction equation

HRID 735082 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][C:9]([OH:11])=O.[Cl:12][C:13]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][C:14]=1[O:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20].ClCCl.CO.N>>[ClH:12].[Cl:12][C:13]1[CH:26]=[C:25]([NH:27][C:9](=[O:11])[C:8]#[C:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:24]=[CH:23][C:14]=1[O:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20]

Participants

4

Reactant 3

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 21584172Ammonia methanol dichloromethaneHCID 454898773-(Pyridin-2-yl)propiolic acid

Product 1

HCID 688195013-pyridin-2-ylpropynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

Procedure

Prepared analogously to Example 2.3.f. from pyridin-2-ylpropynoic acid and [2-(2-chloro-4-aminophenoxy)ethyl]diethylamine. Yield: 0.37 g (53.3% of theory); C20H22ClN3O2*HCl (M=408.33); calc.: molecular ion peak (M+H)+: 372/374; found: molecular ion peak (M+H)+: 372/374; Rf value: 0.5 (silica gel, dichloromethane/methanol/ammonia (9:1:0.1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-08012dac568a43ab93b470d47a47e5d8
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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