Diisopropylethylamine → Methyl 6-[([1,1'-biphenyl]-2-carbonyl)amino]-pyridine-3-carboxylate

HRID 863042Notes

Reaction equation

HRID 863042 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22]([C:27](Cl)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>C(Cl)Cl>[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22]([C:27]([NH:1][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=2)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 737487Methyl 6-aminonicotinateHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 22099771Methyl 6-[([1,1'-biphenyl]-2-carbonyl)amino]-pyridine-3-carboxylateYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.5 g of methyl 6-amino-pyridine-3-carboxylate in 100 ml of methylene chloride is added 3 ml of N,N-diisopropylethylamine at room temperature. To the stirred reaction mixture is slowly added a solution of 2.5 g of [1,1'-biphenyl]-2-carbonyl chloride. The reaction mixture is stirred at room temperature for 4 hours and then quenched with water. The organic layer is washed well with water and dried over anhydrous MgSO4, filtered and evaporated in vacuo to a solid residue. The residue is stirred with ether, filtered and dried to give 3.0 g of the desired product: M+ =332.

Workup

  1. customTo the stirred reaction mixture
  2. customquenched with water
  3. washThe organic layer is washed well with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo to a solid residue
  7. stirringThe residue is stirred with ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-09c6ae32f7ac4f1dbb9acb822456bda6
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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