Diisopropylethylamine → Methyl 6-[[bis(2-biphenylcarbonyl)]amino]pyridine-3-carboxylate

HRID 1940783Notes

Reaction equation

HRID 1940783 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([CH:18]([CH3:20])[CH3:19])CC)(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>ClCCl.O>[C:23]1([C:19]2[CH:18]=[CH:20][CH:35]=[CH:30][CH:31]=2)[C:22]([C:27]([N:1]([C:27]([C:22]2[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:28])[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:21][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

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

Product 1

HCID 22099573Methyl 6-[[bis(2-biphenylcarbonyl)]amino]pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a chilled (0° C.) solution of 2.64 g of methyl 6-aminopyridine-3-carboxylate and 5.5 ml of diisopropylethylamine in 30 ml of dichloromethane under argon is added 6.8 g of 2-biphenylcarbonyl chloride in 10 ml of dichloromethane. The mixture is stirred at room temperature 2 days and then diluted with 120 ml of dichloromethane and 50 ml of water. The organic layer is separated, washed with 50 ml each of 1M NaHCO3 and brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated under vacuum to give a solid. Crystallization from ethyl acetate gives 6.2 g of white crystals, m.p. 180°-188° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 50 ml each of 1M NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated under vacuum
  6. customto give a solid
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4a407c9c19f6470b8455fe8f6749b859
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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