Sodium Hydroxide → 2-(1,1-difluoroethyl)-N-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-amine

HRID 1987216Notes

Reaction equation

HRID 1987216 reaction equation
[F:1][C:2]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([N:21](C)[C:22](=O)C)=[CH:20][C:7]=2[N:6]=1)([F:4])[CH3:3].[OH-].[Na+]>Cl>[F:4][C:2]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:8]2[CH:17]=[CH:18][C:19]([NH:21][CH3:22])=[CH:20][C:7]=2[N:6]=1)([F:1])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57441091N-[2-(1,1-Difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-methylacetamide

Product 1

HCID 577232152-(1,1-difluoroethyl)-N-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

N-[2-(1,1-Difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-methylacetamide (0.48 g, 1.37 mmol) was heated to 80° C. overnight in concentrated HCl (80 mL). The reaction mixture was cool to 0° C. and brought to slightly basic pH using NaOH solution. The compound was extracted with EtOAc (3×) and the combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The solvent was concentrated giving the title compound that was used for the next step without further purification. Yield: 0.42 g (98%); MS (ESI) (M+H)+: 310.2.

Workup

  1. extractionThe compound was extracted with EtOAc (3×)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-11a9ac44d7104c28948d542c1b700ae3
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

Loading…