Triethylamine → HCID 90460107, compound

HRID 588833Notes

Reaction equation

HRID 588833 reaction equation
[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:19][N:18]([C:20](OC(C)(C)C)=[O:21])[CH2:17]3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([O:30][CH3:31])[CH:3]=1.[CH2:32](N(CC)CC)[CH3:33].C(Cl)(=O)C=C>Cl.CO.C(Cl)Cl>[C:20]([N:18]1[CH2:17][CH:16]([N:13]2[CH2:14][CH2:15][CH:10]([C:8]([NH:7][CH2:6][C:5]3[CH:27]=[C:28]([Cl:29])[C:2]([Cl:1])=[CH:3][C:4]=3[O:30][CH3:31])=[O:9])[CH2:11][CH2:12]2)[CH2:19]1)(=[O:21])[CH:32]=[CH2:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 90460454HCID 90460454, compound

Product 1

HCID 90460107HCID 90460107, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of tert-butyl 3-(4-(4,5-dichloro-2-methoxybenzylcarbamoyl)piperidin-1-yl)azetidine-1-carboxylate (210 mg, 0.44 mmol) in HCl/MeOH (10 mL, 2.86 M) was stirred at room temperature for 1 h. The mixture was concentrated in vacuo to yield the crude residue. The residue was dissolved in DCM (5 mL), triethylamine (0.5 mL) and acryloyl chloride (40 mg, 0.43 mmol) were added. The reaction mixture was stirred at room temperature for 30 min and then partitioned between DCM and water. The organic layer was washed with water and 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 (150 mg, 82% yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto yield the crude residue
  3. stirringThe reaction mixture was stirred at room temperature for 30 min
  4. custompartitioned between DCM and water
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-10569a0444254330b226ac94496e4ab1
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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