Benzylamine → HCID 178522817, compound

HRID 18618Notes

Reaction equation

HRID 18618 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=[O:24].[Na+]>O1CCCC1.O>[CH2:15]([NH:22][C:9]([C:7]1[NH:6][C:5]2[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 178477904HCID 178477904, compound

Product 1

HCID 178522817HCID 178522817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 120.0 mg (0.45 mmol) 5-chloro-2-trichloromethyl-1H-benzoimidazole in 2 mL tetrahydrofuran (THF) was added slowly to a mixture of 53.5 μl (0.49 mmol) benzylamine and 373.8 mg (4.45 mmol, 10 equiv.) NaHCO3 in 8 mL THF and 4 mL water. The reaction mixture was stirred for 2 h at room temperature (20° C. to 25° C. in the following RT). The suspension was filtered and the filtrate was concentrated under reduced pressure. After purification by preparative RP-HPLC (CH3CN/H2O gradient and 0.05% formic acid) pure 5-Chloro-1H-benzoimidazole-2-carboxylic acid benzylamide was obtained as a white amorphous solid.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customAfter purification by preparative RP-HPLC (CH3CN/H2O gradient and 0.05% formic acid) pure 5-Chloro-1H-benzoimidazole-2-carboxylic acid benzylamide
  4. customwas obtained as a white amorphous solid

Sources & evidence

ORD record
ord-9120dfe3e18d4563af9733c833b8e68a
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

Loading…