Sodium Bicarbonate → HCID 178497373, compound

HRID 18513Notes

Reaction equation

HRID 18513 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:17]=[CH:16][C:8]2[NH:9][C:10]([C:12](Cl)(Cl)Cl)=[N:11][C:7]=2[CH:6]=1)=[O:4].Cl.Cl.[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].C([O-])(O)=[O:31].[Na+]>C1COCC1.O.ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:17]=[CH:16][C:8]2[NH:9][C:10]([C:12](=[O:31])[NH:29][CH:26]3[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]3)=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideHCID 178497356HCID 178497356, compound

Product 1

HCID 178497373HCID 178497373, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg (1.7 mmol) Methyl-2-trichloromethyl-1H-benzoimidazole-5-carboxylate were added to a mixture of 548 mg (1.8 equiv.) 1-isopropyl-piperidine-4-ylamine-dihydrochloride and 1.43 g (10 equiv.) NaHCO3 in 15 mL THF and 7.5 mL H2O and stirred vigorously for 4 h at room temperature. The reaction mixture was diluted with dichloromethane and washed with a saturated NaHCO3-solution and brine. The organic layer was dried over MgSO4 and concentrated. Preparative HPLC (CH3CN/H2O gradient+0.05% formic acid) gave pure 2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a white solid.

Workup

  1. washwashed with a saturated NaHCO3-solution and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1b867e3858314c57807212d369590eeb
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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