Water → HCID 86603686, compound

HRID 226381Notes

Reaction equation

HRID 226381 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[N:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=2)[CH2:4]1.C(N(CC)CC)C.[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1.O>CN(C=O)C>[Cl:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([N:3]2[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]3[N:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=3)[CH2:4]2)=[O:36])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 86603687HCID 86603687, compound

Product 1

HCID 86603686HCID 86603686, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl (2E)-3-{6-[(3R)-3-piperidinylamino]-3-pyridinyl}acrylate dihydrochloride (300 mg, 0.86 mmol) in DMF (4 mL) were added triethylamine (349 mg, 3.45 mmol) and 4-chlorobenzoyl chloride (181 mg, 1.03 mmol) at 0° C. under nitrogen and the mixture was stirred at same temperature for 1 hr and at ambient temperature for 2 hrs. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (hexane-EtOAc=1-1) to give ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-piperidinyl]amino}-3-pyridinyl)acrylate (270 mg, 76%) as an amorphous powder.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (hexane-EtOAc=1-1)

Sources & evidence

ORD record
ord-0e337c45a41141b8bd4b3b2a46766857
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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