Sodium Carbonate → HCID 59585983, compound

HRID 1628838Notes

Reaction equation

HRID 1628838 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:16]=[CH:17][C:18]([OH:22])=[N:19][C:20]=4[CH3:21])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([O:28][CH:29]([F:31])[F:30])[C:24]([F:27])([F:26])[F:25])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:38][C:39]([F:47])(S(F)(=O)=O)C(O)=O>C(#N)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:20]([CH3:21])=[N:19][C:18]([O:22][CH:39]([F:47])[F:38])=[CH:17][CH:16]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([O:28][CH:29]([F:30])[F:31])[C:24]([F:27])([F:26])[F:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178433442HCID 178433442, compound

Product 1

HCID 59585983HCID 59585983, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-{9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl}-6-methylpyridin-2-ol (90.0 mg, 0.194 mmol) in acetonitrile (2.0 mL) was added sodium carbonate (41.1 mg, 0.389 mmol) and 2,2-difluoro-2-fluorosulfonyl-aceticacid (40.2 μL, 0.389 mmol) 0° C. The reaction mixture was stirred at room temperature for 1.5 hrs. The mixture was concentrated. The precipitate was removed by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography eluting with a 0-35% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless powder (77.3 mg, 0.151 mmol, 78%).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with a 0-35% ethyl acetate/n-hexane gradient mixture
  6. customThe resulting solid was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ae0041e9dffd4fd9a658169968438ea7
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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