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

HRID 859794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859794
ClC1C=C(C(Cl)=O)C=CN=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:35]=[CH:36][N:37]=1)[C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:34])=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=2)[CH:23]=1)=[O:16].NC1C=CC(C)=C(C2C=CC(C(OC)=O)=CC=2)C=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:35]=[CH:36][N:37]=1)[C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:34])=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:29]=2)[CH:23]=1)=[O:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 21090583Methyl 5'-amino-2'-methyl-1,1'-biphenyl-4-carboxylateHCID 86595281Methyl 5'-[(2-chloroisonicotinoyl)amino]-2'-methyl-1,1'-biphenyl-4-carboxylate 2-Chloropyridine-4-carbonyl chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methyl 5′-[(2-chloroisonicotinoyl)amino]-2′-methyl-1,1′-biphenyl-4-carboxylate 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%). LCMS: retention time 3.69 min, MH+381.

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-dfe4dd1ce735440282b080a72c2f5d19
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151118B2

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