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

HRID 351291Notes

Reaction equation

HRID 351291 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-403a0796b89044c09e0af0763813b1a3
Source dataset
uspto-grants-2007_02
Patent number
US07183297B2

Reaction notes

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