Water → HCID 178527411, compound

HRID 1506176Notes

Reaction equation

HRID 1506176 reaction equation
I[CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[N:10]=[N:11][N:12]3[C:17]=2[C:16]2[CH:18]=[CH:19][NH:20][C:15]=2[N:14]=[CH:13]3)[CH2:5][CH2:4]1.[F:21][C:22]([S:25]([O-:27])=[O:26])([F:24])[F:23].[Na+].O>CN(C)C=O>[F:21][C:22]([F:24])([F:23])[S:25]([CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[N:10]=[N:11][N:12]3[C:17]=2[C:16]2[CH:18]=[CH:19][NH:20][C:15]=2[N:14]=[CH:13]3)[CH2:5][CH2:4]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 23690734Sodium trifluoromethanesulfinateHCID 178506580HCID 178506580, compound

Product 1

HCID 178527411HCID 178527411, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[trans-4-(Iodomethyl)cyclohexyl]-7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidine (50.0 mg, 0.131 mmol) and sodium trifluoromethylsulfinate (205 mg, 1.31 mmol) in N,N-dimethylformamide (3 mL) were stirred at 100° C. for 26 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2→1/1 (v/v)) and preparative HPLC (Waters XBridge Prep C18 μm ODS, 19×100 mm, acetonitrile/0.1% aqueous formic acid solution=20/80→80/20(v/v)) to give the title compound as a colorless solid (6.30 mg, yield 12%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2→1/1 (v/v)) and preparative HPLC (Waters XBridge Prep C18 μm ODS, 19×100 mm, acetonitrile/0.1% aqueous formic acid solution=20/80→80/20(v/v))

Sources & evidence

ORD record
ord-e0ce9532eb88440e92e5980a82ed5377
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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