Water → HCID 90460666, compound

HRID 588824Notes

Reaction equation

HRID 588824 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11](OC)=[C:10]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27]C(C)(C)C)=O)[CH2:21][CH2:20]2)=[O:18])[CH:9]=1.[CH2:32](N(CC)CC)[CH3:33].[C:39](Cl)(=O)C=C.[OH2:44]>Cl.CO.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([O:44][CH3:39])=[C:10]([C:17]([N:19]2[CH2:20][CH2:21][N:22]([C:25](=[O:27])[CH:32]=[CH2:33])[CH2:23][CH2:24]2)=[O:18])[CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 117607168HCID 117607168, compound

Product 1

HCID 90460666HCID 90460666, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2′,6-dichloro-4-methoxy-[1,1′-biphenyl]-3-carbonyl)piperazine-1-carboxylate (200 mg, 0.43 mmol) was stirred in HCl in MeOH (2.86 M, 10 mL) for 1 h. The mixture was concentrated in vacuo to yield the crude product. The residue was dissolved in DCM (15 mL), triethylamine (0.5 mL), acryloyl chloride (40 mg, 0.43 mmol) was added to the mixture. The reaction mixture was stirred at room temperature for 30 min, poured into water, and extracted with DCM. 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 (16 mg, 10% yield) as white solid. ESI-MS m/z: 419.2[M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto yield the crude product
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-4e4098a57d3041298b9ee68eb0dd4e7e
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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