HOAt → 2-Chloro-5-[(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-amino]-benzoic acid methyl ester

HRID 1919605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919605
[CH3:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.[NH2:37][C:38]1[CH:39]=[CH:40][C:41]([Cl:48])=[C:42]([CH:47]=1)[C:43]([O:45][CH3:46])=[O:44]>CN(C)C=O.O>[CH3:46][O:45][C:43](=[O:44])[C:42]1[CH:47]=[C:38]([NH:37][C:4]([C:3]2[C:2]([CH3:1])=[N:10][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=2)=[O:6])[CH:39]=[CH:40][C:41]=1[Cl:48]

Komponenten

7

Edukt 4

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27756832-Methyl-6-(trifluoromethyl)nicotinic acidHCID 5200412Methyl 5-Amino-2-chlorobenzoate

Produkt 1

HCID 323079312-Chloro-5-[(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-amino]-benzoic acid methyl esterAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 2-methyl-6-trifluoromethylnicotinic acid (4.77 g; 23 mmol) in dimethyl formamide (100 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.46 g; 23 mmol) and 1-hydroxy-7-azabenzotriazole (3.17 g; 23 mmol) and the resulting solution was stirred at room temperature for 30 minutes. To this was added a solution of methyl 5-amino-2-chlorobenzoate (3.6 g; 19 mmol) in dimethyl formamide (25 ml) and the resulting solution stirred at room temperature for 18 hours. Water (200 ml) was added to the reaction mixture and this was extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with saturated sodium bicarbonate solution (2×300 ml). The organic layer was dried (magnesium sulphate), filtered and evaporated to give 2-chloro-5-[(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-amino]-benzoic acid methyl ester (6.6 g, 94%).

Aufarbeitung

  1. stirringthe resulting solution stirred at room temperature for 18 hours
  2. extractionthis was extracted with ethyl acetate (3×200 ml)
  3. washThe combined organic layers were washed with saturated sodium bicarbonate solution (2×300 ml)
  4. dry with materialThe organic layer was dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-520673c86e404466aed3f6d184ab8f70
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168653B2

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