Methylamine → 5-amino-2,4-difluoro-N-methylbenzamide

HRID 1985749

Reaktionsgleichung

Reaktionsgleichung von HRID 1985749
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([NH2:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C[CH2:14][N:15]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN>CN(C=O)C.C(OCC)(=O)C>[NH2:12][C:8]1[C:9]([F:11])=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([NH:15][CH3:14])=[O:5]

Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 210494315-Amino-2,4-difluorobenzoic acid

Produkt 1

HCID 220191305-amino-2,4-difluoro-N-methylbenzamideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2,4-difluoro-5-aminobenzoic acid (1.73 g, 10.0 mmol) in DMF (40 mL) were successively added EDCI (1.62 g, 12.0 mmol), HOBt (2.30 g, 12.0 mmol) and methylamine (6.0 mL, 12.0 mmol, 2 M in MeOH) in that order at RT. After stirring for 2 h, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (100 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with NaHCO3 (3×50 mL) followed by 10% LiCl (50 mL). The organic layer was dried, filtered and concentrated to afford 5-amino-2,4-difluoro-N-methylbenzamide (0.76 g, 41%) as a light brownish solid. MS (M+H)+=187. It was used without further purification (>92% pure by HPLC).

Aufarbeitung

  1. customat RT
  2. washwashed with water (100 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layer was washed with NaHCO3 (3×50 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-758ff639c5524fcc84d65d9776a3ed30
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547711B2

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