Triethylamine → Methyl 5'-[(2-chloroisonicotinoyl)amino]-2'-methyl-1,1'-biphenyl-4-carboxylate

HRID 351291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351291
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=2)[CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=2)[CH:17]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 21090583Methyl 5'-amino-2'-methyl-1,1'-biphenyl-4-carboxylate

Produkt 1

HCID 21090582Methyl 5'-[(2-chloroisonicotinoyl)amino]-2'-methyl-1,1'-biphenyl-4-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Chloropyridine-4-carbonyl chloride (1.58 g, 9.0 mmol) in DCM (10 ml) was added dropwise to a solution of methyl 5′-amino-2′-methyl-1,1′-biphenyl-4-carboxylate (1.81 g, 7.5 mmol) and triethylamine (3.13 ml, 22.5 mmol) in DCM (10 ml) at 0° C. The reaction was stirred at room temperature for 20 h, the solvent evaporated under vacuum and the residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate (50 ml). The aqueous was extracted with ethyl acetate (50 ml) and the combined organic phases washed with brine (50 ml), dried (magnesium sulphate) and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica eluting with DCM/ethanol/ammonia (300:8:1). The solvents were evaporated under vacuum to give methyl 5′-[(2-chloroisonicotinoyl)amino]-2′-methyl-1,1′-biphenyl-4-carboxylate (1.73 g, 61%).

Aufarbeitung

  1. customthe solvent evaporated under vacuum
  2. customthe residue partitioned between ethyl acetate (50 ml) and saturated aqueous sodium bicarbonate (50 ml)
  3. extractionThe aqueous was extracted with ethyl acetate (50 ml)
  4. washthe combined organic phases washed with brine (50 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent evaporated under vacuum
  7. customThe residue was purified by flash column chromatography on silica eluting with DCM/ethanol/ammonia (300:8:1)
  8. customThe solvents were evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-403a0796b89044c09e0af0763813b1a3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183297B2

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