Bis(2-oxo-3-oxazolidinyl)phosphinic chloride → 1H-Benzoimidazole-2-carboxylic acid (1-pyrimidin-4-yl-piperidin-4-yl)-amide

HRID 18511

Reaction equation

HRID 18511 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.FC(F)(F)C(O)=O.[N:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]2)=[N:22][CH:21]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCN(CC)CC>[N:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:27][CH2:28][CH:29]([NH:32][C:10]([C:2]3[NH:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:12])[CH2:30][CH2:31]2)=[N:22][CH:21]=1

Participants

7

Reactant 4

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2332402-Benzimidazolecarboxylic acidHCID 516892Sodium BicarbonateHCID 223943841-Pyrimidin-4-yl-piperidin-4-ylamine trifluoroacetate

Product 1

HCID 860098671H-Benzoimidazole-2-carboxylic acid (1-pyrimidin-4-yl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 80 mg 1H-Benzoimidazole-2-carboxylic acid in 1 mL DMF and 0.2 mL NEt3, 200 mg 1-Pyrimidin-4-yl-piperidin-4-ylamine trifluoroacetate and 125 mg BOP-Cl were added and the mixture was stirred for 3 h. Finally, 3 mL saturated NaHCO3 solution were added and the mixture was filtered through a chem elut® cartridge by elution with ethyl acetate. After removal of the solvent under reduced pressure the crude product was subjected to the next reaction step without further purification. Yield: 160 mg.

Workup

  1. filtrationthe mixture was filtered through a chem elut® cartridge by elution with ethyl acetate
  2. customAfter removal of the solvent under reduced pressure the crude product
  3. customwas subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-79f71b05143e49688872fd3f6a5d773c
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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