N-Methyl-N-[1-(tetrahydro-2H-pyran-4-ylmethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-yl]acetamide → HCID 57441079, compound

HRID 1987205Notes

Reaction equation

HRID 1987205 reaction equation
[CH3:1][N:2]([C:6]1[CH:25]=[CH:24][C:9]2[N:10]([CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:11]([C:13]([F:16])([F:15])[F:14])=[N:12][C:8]=2[CH:7]=1)C(=O)C>Cl>[CH3:1][NH:2][C:6]1[CH:25]=[CH:24][C:9]2[N:10]([CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:11]([C:13]([F:14])([F:15])[F:16])=[N:12][C:8]=2[CH:7]=1

Participants

3

Reactant 1

HCID 57723217N-Methyl-N-[1-(tetrahydro-2H-pyran-4-ylmethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-yl]acetamide

Product 1

HCID 57441079HCID 57441079, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

N-Methyl-N-[1-(tetrahydro-2H-pyran-4-ylmethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-yl]acetamide (3.18 g, 8.95 mmol) was dissolved in hydrochloric acid (37%, 60 mL) and then heated overnight at 95° C. After concentration, the residue was treated with 20 mL of 2N NaOH, extracted with EtOAc (4×50 mL). The combined organic phases were washed with brine (20 mL) and dried over Na2SO4. After evaporation, 2.80 g (100%) of a purple white solid was obtained as the title product, which was used directly for Step H. MS (ESI) (M+H)+=314.20.

Workup

  1. concentrationAfter concentration
  2. additionthe residue was treated with 20 mL of 2N NaOH
  3. extractionextracted with EtOAc (4×50 mL)
  4. washThe combined organic phases were washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-16d413d6a65840bbba38e1eb5e6fa2a7
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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