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Trifluoroacetic acid → 1-(4-(3-Amino-4-cyanoisothiazol-5-yl)phenyl)-3-(2-fluoro-5-methylphenyl)urea

HRID 871005
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 871005
[C:1]([C:3]1[C:4]([NH:26]CC2C=CC(OC)=CC=2OC)=[N:5][S:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=2[F:25])=[O:16])=[CH:10][CH:9]=1)#[N:2].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:26][C:4]1[C:3]([C:1]#[N:2])=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=3[F:25])=[O:16])=[CH:10][CH:9]=2)[S:6][N:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 866892251-(4-{4-Cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea

Produkt 1

HCID 866892261-(4-(3-Amino-4-cyanoisothiazol-5-yl)phenyl)-3-(2-fluoro-5-methylphenyl)ureaAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A suspension of 1-(4-{4-cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea (593 mg, 1.15 mmol) in 50 mL of DCM was treated with 1.5 mL of TFA. Solid was dissolved and the reaction turned to yellow and then red in color. TLC indicated the completion of the reaction in <30 min. Saturated Na2CO3 solution was added and the mixture was stirred for 30 min. Layers were separated and the aqueous layer was extracted with DCM×3. The combined organics was washed with brine and dried with MgSO4, filtered, and concentrated. The crude product was redissolved in 100 mL of EtOAc. Insoluble impurity was filtered through celite and washed with EtOAc. Filtrate was concentrated in vacuo to afford the product as a cream solid (398 mg, 94%).

Aufarbeitung

  1. dissolutionSolid was dissolved
  2. customthe completion of the reaction in <30 min
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with DCM×3
  5. washThe combined organics was washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe crude product was redissolved in 100 mL of EtOAc
  10. filtrationInsoluble impurity was filtered through celite
  11. washwashed with EtOAc
  12. concentrationFiltrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d1845d110ce4c80934a998bf05538fb
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969583B2

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