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Formaldehyde → N-{4-(4-bromo-2-fluoro-phenylamino)-7-[2-(2-dimethylamino-propionylamino)-ethoxy]-quinazolin-6-yl}-acrylamide

HRID 81455
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 81455
N[CH:2]([CH3:33])[C:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[F:27])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[NH:28][C:29](=[O:32])[CH:30]=[CH2:31])=[O:4].[CH2:34]=O.[C:36]([BH3-])#[N:37].[Na+]>C1COCC1.CO>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([O:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH:2]([N:37]([CH3:36])[CH3:34])[CH3:33])=[C:10]([NH:28][C:29](=[O:32])[CH:30]=[CH2:31])[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[C:21]([F:27])[CH:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16678543N-[7-[2-(2-amino-propionylamino)-ethoxy]-4-(4-bromo-2-fluoro-phenylamino)-quinazolin-6-yl]-acrylamide

Produkt 1

HCID 16679451N-{4-(4-bromo-2-fluoro-phenylamino)-7-[2-(2-dimethylamino-propionylamino)-ethoxy]-quinazolin-6-yl}-acrylamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-[7-[2-(2-amino-propionylamino)-ethoxy]-4-(4-bromo-2-fluoro-phenylamino)-quinazolin-6-yl]-acrylamide (30 mg, 0.06 mmol) and 37 weight % of formaldehyde (9 μl, 0.12 mmol) were diluted with THF (1 ml) and methanol (1 ml), and stirred at room temperature for 10 min. Sodium cyanoborohydride (11 mg, 0.17 mmol) was added thereto, and the solution was stirred for 4 hours. The resulting solution was distilled under a reduced pressure to remove the solvent, saturated sodium bicarbonate aqueous solution (20 ml) was added thereto, and extracted with chloroform (20 ml) twice. The separated organic layer was dried over magnesium sulfate, filtered and distilled under a reduced pressure, and resulting impure residue was subjected to column chromatography to obtain the title compound 23 mg (yield: 73%).

Aufarbeitung

  1. stirringthe solution was stirred for 4 hours
  2. distillationThe resulting solution was distilled under a reduced pressure
  3. customto remove the solvent, saturated sodium bicarbonate aqueous solution (20 ml)
  4. additionwas added
  5. extractionextracted with chloroform (20 ml) twice
  6. dry with materialThe separated organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure
  9. customresulting impure residue

Quellen und Nachweise

ORD-Eintrag
ord-997f1c4d2fe946ed96883f8c9eb2b539
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846699B2

Notizen zur Reaktion

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