Triethylamine → HCID 90455895, compound

HRID 588885Notes

Reaction equation

HRID 588885 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]2[C:18](=[O:20])[NH2:19])[CH2:2]1.CCN(CC)CC.[C:28](Cl)(=[O:31])[CH:29]=[CH2:30]>C(Cl)Cl>[C:28]([N:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][CH:6]2[C:18](=[O:20])[NH2:19])[CH2:2]1)(=[O:31])[CH:29]=[CH2:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 90460818HCID 90460818, compound

Product 1

HCID 90455895HCID 90455895, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(azetidin-3-yl)-3-carbamoylpiperazine-1-carboxylate (640 mg, 2.22 mmol) and Et3N (463 mg, 4.58 mmol) in DCM (10 mL) at 0° C., acryloyl chloride (248 mg, 2.74 mmol) was added dropwise and the resulting mixture was stirred at RT for 1.5 h. The mixture was partitioned between dichloromethane and saturated NaHCO3 solution. The organic layer was washed with saturated brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the desired product (350 mg, 47% yield).

Workup

  1. customThe mixture was partitioned between dichloromethane and saturated NaHCO3 solution
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-a904c21f51864fbe8f2119a9a2b0fbb7
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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