1,2-Dichloroethane → ethyl 4-[2-[1-[3-methoxy-4-(N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethynyl]benzoate

HRID 350340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350340
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:35]#[C:36][CH:37]2[CH2:41][CH2:40][CH2:39][NH:38]2)=[CH:31][CH:30]=1)=[O:28])[CH3:25].C(Cl)CCl.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:38]2[CH2:39][CH2:40][CH2:41][CH:37]2[C:36]#[C:35][C:32]2[CH:33]=[CH:34][C:29]([C:27]([O:26][CH2:24][CH3:25])=[O:28])=[CH:30][CH:31]=2)=[O:23])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 235119142-(2-(4-Ethoxycarbonylphenyl)ethynyl)pyrrolidine

Produkt 1

HCID 69332958ethyl 4-[2-[1-[3-methoxy-4-(N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethynyl]benzoateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (1.45 g, 4.6 mmol), 2-(2-(4-ethoxycarbonylphenyl)ethynyl)pyrrolidine (1.12 g, 4.6 mmol), EDC 1.32 g (6.9 mmol), DMAP (562 mg, 4.6 mmol) in DMF (20 ml-) was stirred overnight. The mixture was poured into 1 N HCl and the solid was collected with suction. The solid was dissolved in CHCl3 and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica-gel with CHCl3-MeOH (100:1, v/v) as eluent to give 2.20 g (89%) ethyl 4-[2-[1-[3-methoxy-4-(N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethynyl]benzoate as a white amorphous solid.

Aufarbeitung

  1. customthe solid was collected with suction
  2. dissolutionThe solid was dissolved in CHCl3
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent
  5. customthe residue was chromatographed on silica-gel with CHCl3-MeOH (100:1

Quellen und Nachweise

ORD-Eintrag
ord-6d01f88c2b54418c9d63fa9bd09d31b3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

Notizen zur Reaktion

Wird geladen…