N-{5-[Acetyl(methyl)amino]-2-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-2,2-difluoropropanamide → N-[2-(1,1-Difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-methylacetamide

HRID 1987215Notes

Reaction equation

HRID 1987215 reaction equation
[C:1]([N:4]([CH3:26])[C:5]1[CH:6]=[CH:7][C:8]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:9]([NH:11][C:12](=O)[C:13]([F:16])([F:15])[CH3:14])[CH:10]=1)(=[O:3])[CH3:2]>C(O)(=O)C>[F:15][C:13]([C:12]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]2[CH:7]=[CH:6][C:5]([N:4]([CH3:26])[C:1](=[O:3])[CH3:2])=[CH:10][C:9]=2[N:11]=1)([F:16])[CH3:14]

Participants

3

Reactant 1

HCID 57441090N-{5-[Acetyl(methyl)amino]-2-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-2,2-difluoropropanamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-{5-[Acetyl(methyl)amino]-2-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-2,2-difluoropropanamide (1.00 g, 2.70 mmol) was heated to 90° C. overnight in acetic acid (20 mL). The solvent was concentrated. The crude product was purified by flash chromatography on silica gel, using MeOH 3.5% and acetone 8% in DCM as eluent, giving the title compound. Yield: 0.48 g (50%); MS (ESI) (M+H)+: 352.0.

Workup

  1. concentrationThe solvent was concentrated
  2. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-775f6aaecf28402dbefc14e92647f11c
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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