4-Chloro-1,2-diaminobenzene → N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide

HRID 1500948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500948
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[F:10][C:11]([F:20])([F:19])[C:12]([OH:18])([CH3:17])[CH2:13][C:14](O)=[O:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[NH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:14](=[O:15])[CH2:13][C:12]([OH:18])([CH3:17])[C:11]([F:20])([F:19])[F:10]

Komponenten

7

Edukt 4

HCID 72634-Chloro-1,2-diaminobenzeneHCID 81531DiisopropylethylamineHCID 1361684,4,4-Trifluoro-3-hydroxy-3-methylbutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 89924350N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamideAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-chlorobenzene-1,2-diamine (1.32 g, 9.3 mmol), 4,4,4-trifluoro-3-hydroxy-3-methylbutanoic acid (1.6 g, 9.3 mmol), HATU (4.24 g, 11.2 mmol), DIPEA (3.1 mL, 18.6 mmol) and DMF (25 mL) was stirred at room temperature overnight. The mixture was diluted with water (150 mL), and then extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL), and then dried over Na2SO4, then filtered and concentrated. The residue was purified with flash column (30% EtOAc in PE to EtOAc) to give N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide as brown oil (2.1 g, 76%).

Aufarbeitung

  1. extractionextracted with EtOAc (50 mL×3)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with flash column (30% EtOAc in PE to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-48d24de882be453ba1e9a38caa36dca2
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206191B2

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