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Diisopropylethylamine → 5-Amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

HRID 335319
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 335319
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][NH2:15])[CH2:4][CH2:3]1.[NH2:16][C:17]1[C:18]([CH3:27])=[CH:19][C:20]([F:26])=[C:21]([CH:25]=1)[C:22](O)=[O:23].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:16][C:17]1[C:18]([CH3:27])=[CH:19][C:20]([F:26])=[C:21]([CH:25]=1)[C:22]([NH:15][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27955682-(4-Methyl-1-piperazinyl)benzenemethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 790021455-Amino-2-fluoro-4-methylbenzoic Acid

Produkt 1

HCID 866956835-Amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture comprising (2-(4-methylpiperazin-1-yl)phenyl)methanamine (413 mg, 2.010 mmol) and 5-amino-2-fluoro-4-methylbenzoic acid (step 2) (340 mg, 2.010 mmol) in DMF (3 ml) was treated with DIPEA (0.351 ml, 2.010 mmol) followed by HATU (764 mg, 2.010 mmol) and stirred at 25° C. for 24 hrs. The mixture was partitioned between water and EtOAc. The organic portion was washed with sat. aq. NaHCO3, 0.5 M LiCl and brine (each back extracted with EtOAc). The combined organic layers were dried (MgSO4), filtered and evaporated to dryness to give a pink oil. Purification by chromatography on silica eluting with 0-20% MeOH in DCM afforded the title compound;

Aufarbeitung

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic portion was washed with sat. aq. NaHCO3, 0.5 M LiCl and brine (each back
  3. extractionextracted with EtOAc)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto give a pink oil
  8. customPurification by chromatography on silica eluting with 0-20% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-1ae9bf6293c343478c2851864051ba76
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883819B2

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