Sodium Methoxide → HCID 89691264, compound

HRID 2203091Notes

Reaction equation

HRID 2203091 reaction equation
Cl.[CH:2]1([C:5]2[N:9]([CH3:10])[C:8]3[CH:11]=[C:12]([N:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23](=[NH:25])[NH2:24])=[CH:17][C:16]4=[O:26])[CH:13]=[CH:14][C:7]=3[N:6]=2)[CH2:4][CH2:3]1.F[P-](F)(F)(F)(F)F.[Cl:34][C:35](=[CH:40]N(C)C)[CH:36]=[N+](C)C.C[O-].[Na+]>CO>[Cl:34][C:35]1[CH:36]=[N:25][C:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][N:15]([C:12]3[CH:13]=[CH:14][C:7]4[N:6]=[C:5]([CH:2]5[CH2:4][CH2:3]5)[N:9]([CH3:10])[C:8]=4[CH:11]=3)[C:16](=[O:26])[CH:17]=2)=[N:24][CH:40]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 748906302-Chloro-3-(dimethylamino)-N,N-dimethylprop-2-en-1-iminium hexafluoridophosphate(1-)HCID 89691033HCID 89691033, compound

Product 1

HCID 89691264HCID 89691264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-((1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-2-oxo-1,2-dihydropyridin-4-yl)oxy)ethanimidamide hydrochloride (100 mg), 2-chloro-3-(dimethylamino)-N,N-dimethylprop-2-en-1-iminium hexafluorophosphate (0.82 ml), sodium methoxide (43.3 mg) and MeOH (10 ml) was stirred at room temperature for 1 h. The mixture was concentrated, and the residue was partitioned between EtOAc and water. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (56 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between EtOAc and water
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-64f982d5672947d69216678564675f89
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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