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

HRID 1290940Notes

Reaction equation

HRID 1290940 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-aminopyridine-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-c6571875f0e34e17914e8b73c009f90e
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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