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

HRID 18507

Reaction equation

HRID 18507 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.Cl.[CH:14]([N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)([CH3:16])[CH3:15].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCN(CC)CC>[CH:14]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:10]([C:2]2[NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[O:12])[CH2:19][CH2:18]1)([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2332402-Benzimidazolecarboxylic acidHCID 516892Sodium BicarbonateHCID 230334601-Isopropylpiperidin-4-amine hydrochloride

Product 1

HCID 670127271H-Benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 300 mg 1H-Benzoimidazole-2-carboxylic acid in 3 mL DMF and 1 mL NEt3, 398 mg 1-Isopropyl-piperidin-4-ylamine hydrochloride and 470 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.

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-be01ac0db92847d3925527deccc00814
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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