Water → HCID 178511230, compound

HRID 1506181Notes

Reaction equation

HRID 1506181 reaction equation
[C:1]1([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH:19]=[N:20]O)[CH2:15][CH2:14]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.N12CCCN=C1CCCCC2.O>ClCCl>[C:1]1([C@H:13]2[CH2:14][CH2:15][C@H:16]([C:19]#[N:20])[CH2:17][CH2:18]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 67749Trifluoromethanesulfonic anhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178526347HCID 178526347, compound

Product 1

HCID 178511230HCID 178511230, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans-4-(7H-Pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanecarbaldehyde oxime (37.4 mg, 0.132 mmol) in dichloromethane (3 mL) was mixed with trifluoromethanesulfonic anhydride (24.0 μL, 0.145 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (43.0 μL, 0.289 mmol) and stirred at room temperature for 18 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2 (v/v)) and washed with hexane/ethyl acetate (5/1 (v/v)) to give the title compound as a colorless solid (20.7 mg, yield 59%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2 (v/v))
  6. washwashed with hexane/ethyl acetate (5/1 (v/v))

Sources & evidence

ORD record
ord-c698a913a2d94922b0985c0294e023f8
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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