Sodium Hydroxide → HCID 57785861, compound

HRID 1628985Notes

Reaction equation

HRID 1628985 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3=[N:14][C:15]4[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([CH:22]([O:27][CH:28]([F:30])[F:29])[C:23]([F:26])([F:25])[F:24])[C:16]=4[N:12]3[CH2:11][CH2:10][CH2:9]2)=[C:4]([CH3:31])[CH:3]=1.[CH3:32][S:33]([O-:35])=[O:34].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+].[Cl-].[NH4+]>CS(C)=O.[Cu]I>[Cl:21][C:20]1[C:15]2[N:14]=[C:13]3[N:8]([C:5]4[CH:6]=[CH:7][C:2]([S:33]([CH3:32])(=[O:35])=[O:34])=[CH:3][C:4]=4[CH3:31])[CH2:9][CH2:10][CH2:11][N:12]3[C:16]=2[C:17]([CH:22]([O:27][CH:28]([F:29])[F:30])[C:23]([F:24])([F:25])[F:26])=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 57785911HCID 57785911, compound

Product 1

HCID 57785861HCID 57785861, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-(4-bromo-2-methylphenyl)-9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (200 mg, 0.381 mmol), sodium methanesulfinate (311 mg, 3.04 mmol), L-proline (44.0 mg, 0.382 mmol), sodium hydroxide (30.6 mg, 0.765 mmol) and copper (I) iodide (72.6 mg, 0.381 mmol) in dimethylsulfoxide (2.0 mL) was attired at 110° C. for 4 days. Aqueous ammonium chloride was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture to give the title compound (21.2 mg, 0.040 mmol, 11%) as white amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-dc8b019f733c43b6b3efe698a2c8c41b
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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