Ethyl Acetate → HCID 57942387, compound

HRID 1898163Notes

Reaction equation

HRID 1898163 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=2)(=[O:23])=[O:22])[C:5]([C:8]([C:10]2[C:18]3[O:17][C:16](=[O:19])[NH:15][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+].CCOC(C)=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([C:31]([F:34])([F:32])[F:33])[CH:25]=2)(=[O:23])=[O:22])[C:5]([CH:8]([OH:9])[C:10]2[C:18]3[O:17][C:16](=[O:19])[NH:15][C:14]=3[CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 53239369HCID 53239369, compound

Product 1

HCID 57942387HCID 57942387, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[5-chloro-2-(2-oxo-2,3-dihydro-benzooxazole-7-carbonyl)-pyridin-3-yl]-4-methyl-3-trifluoromethyl-benzenesulfonamide (41 mg) in THF (1 mL) and H2O (0.1 mL) was added NaBH4 (10 mg). The mixture was stirred at room temperature for 1 h, diluted by EtOAc (3 mL) and quenched by saturated aqueous NH4Cl solution (1 mL). The organic layer was separated, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by flash chromatography (silica) to afford the title compound as a white powder. MS (M+H)+: 514.0.

Workup

  1. customquenched by saturated aqueous NH4Cl solution (1 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (silica)

Sources & evidence

ORD record
ord-83694b87527646ac82e839ccc91cc90a
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

Loading…