Dimethylformamide → Methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(4-cyanoanilino)-carbonyl]amino}methyl)phenoxy]acetate

HRID 551906

Reaktionsgleichung

Reaktionsgleichung von HRID 551906
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][CH2:19][C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:34]([C:36]1[CH:41]=[CH:40][C:39]([N:42]=[C:43]=[O:44])=[CH:38][CH:37]=1)#[N:35].C(O)C(N)(CO)CO.CN(C=O)C>C(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=3)[C:43]([NH:42][C:39]3[CH:40]=[CH:41][C:36]([C:34]#[N:35])=[CH:37][CH:38]=3)=[O:44])=[CH:32][CH:33]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6503Tris(hydroxymethyl)aminomethaneHCID 1703804-Cyanophenyl isocyanateHCID 57554567Methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}acetate

Produkt 1

HCID 11621237Methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(4-cyanoanilino)-carbonyl]amino}methyl)phenoxy]acetateAusbeute 132,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]-phenoxy}acetate (37 mg, 0.084 mmol) in anhydrous DCM (2 ml) was added 4-cyanophenyl isocyanate (Aldrich, 45 mg, 0.31 mmol) and the reaction mixture was stirred at rt for 18 hrs. Then PS-trisamine resin (75 mg, Novabiochem, 3.5 mmol/g) and DMF (1 mL) were added and the resulting mixture was stirred at rt for 5 additional hrs. Removal of the resin by filtration followed by evaporation of the solvents gave 65 mg (97%) of the title compound as a pale yellow oil. HPLC, Rt: 5.7 min (purity: 74.1%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at rt for 5 additional hrs
  2. customRemoval of the resin
  3. filtrationby filtration
  4. customfollowed by evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-b7fb90f33d7946b995f6784ce9ebb79e
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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