Dimethylformamide → HCID 67130952, compound

HRID 527968Notes

Reaction equation

HRID 527968 reaction equation
[CH2:1]1[CH2:11]CN2[C:4](=[N:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.[CH3:12][N:13]([CH:15]=[O:16])[CH3:14]>CC(=O)OCC.O>[CH2:11]=[C:1]1[C:2]2=[CH:3][CH:4]=[N:5][C:6]3[CH:7]=[CH:8][C:15](=[O:16])[N:13]([C:14]=32)[CH2:12]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 67130952HCID 67130952, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of intermediate BD.v (1.03 g) in DMF (10 mL) was stirred at rt in the presence of DBU (1.12 mL) for 2 h. The reaction mixture was diluted with EA and water. The aq. layer was extracted with EA (2×100 mL) and DCM/MeOH (3×50 mL; 9:1). The combined org. layers were sequentially washed with water and brine and dried over MgSO4. The solvent was evaporated under reduced pressure, affording a yellow solid (490 mg; 72% yield).

Workup

  1. extractionThe aq. layer was extracted with EA (2×100 mL) and DCM/MeOH (3×50 mL; 9:1)
  2. washlayers were sequentially washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under reduced pressure
  5. customaffording a yellow solid (490 mg; 72% yield)

Sources & evidence

ORD record
ord-dbfef0eee1464719bfd8c2471205259d
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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