ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate → HCID 86583557, compound

HRID 1016787Notes

Reaction equation

HRID 1016787 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([CH2:8][CH3:9])[CH:7]=1.Cl.Cl[CH2:27][CH2:28][NH2:29].Cl[CH2:31][CH2:32]N>ClC1C=CC=CC=1>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([NH:16][CH:10]([C:4]2[CH:3]=[C:2]([N:1]3[CH2:32][CH2:31][NH:29][CH2:28][CH2:27]3)[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:18][CH:19]=1)#[N:24]

Participants

4

Reactant 2

HCID 86583558ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetateHCID 86583559Bis(2-chloroethylamine) hydrochloride

Product 1

HCID 86583557HCID 86583557, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (500 mg, 1.55 mmol) obtained in Example 223.4, bis-(2-chloroethylamine) hydrochloride (276 mg, 1.55 mmol) and chlorobenzene (5 ml) was heated under reflux for 18 h. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1). There were obtained 385 mg (63%) of ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-5-piperazin-1-yl-phenyl)-acetate as a brownish solid; MS: 393 ([M+H]+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-6c0c5988877f434180b5b27a45ef9675
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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