Dimethylformamide → 3-[[(2R)-Tetrahydro-2-furanyl]methyl]-5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-thiadiazol-2(3H)-imine

HRID 452939Notes

Reaction equation

HRID 452939 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1([C:6]2[S:10][C:9]([NH2:11])=[N:8][N:7]=2)[CH2:5][CH2:4]1.CN(C)[CH:16]=[O:17]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:17]1[CH2:16][CH2:5][CH2:4][C@@H:3]1[CH2:2][N:8]1[N:7]=[C:6]([C:3]2([C:2]([F:1])([F:12])[F:13])[CH2:5][CH2:4]2)[S:10][C:9]1=[NH:11]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 675442031140917-14-1

Product 1

HCID 675451643-[[(2R)-Tetrahydro-2-furanyl]methyl]-5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-thiadiazol-2(3H)-imine

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

A mixture of Example 1A (0.15 g, 0.7 mmol), Example 1B (0.20 g, 0.8 mmol) and tetrabutylammonium iodide (0.13 g, 0.36 mmol) in N,N-dimethylformamide (0.2 mL) was heated at 95° C. for 16 hr, cooled to room temperature and quenched with 1M NaHCO3 (10 mL). The aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford 0.2 g (crude) of the title compound. LC/MS (ESI+) m/z 294 (M+H)+.

Workup

  1. customwas heated at 95° C. for 16 hr
  2. customquenched with 1M NaHCO3 (10 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (3×10 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-883a66c88a8a43898494bf3bc7785771
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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