Potassium Iodide → Methyl 5-{[(4-{2-[3-(aziridin-1-ylcarbonyl)phenyl]ethyl}piperidin-1-yl)carbonyl]oxy}nicotinate

HRID 605805Notes

Reaction equation

HRID 605805 reaction equation
CN(C=O)C.Br[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]3[CH:30]=[N:31][CH:32]=[C:33]([CH:38]=3)[C:34]([O:36][CH3:37])=[O:35])=[O:27])[CH2:22][CH2:21]2)[CH:15]=[CH:16][CH:17]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CCOC(C)=O>[N:9]1([C:10]([C:12]2[CH:13]=[C:14]([CH2:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]4[CH:30]=[N:31][CH:32]=[C:33]([CH:38]=4)[C:34]([O:36][CH3:37])=[O:35])=[O:27])[CH2:22][CH2:21]3)[CH:15]=[CH:16][CH:17]=2)=[O:11])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 57507765Methyl 5-[{(4-[2-(3-{[(2-bromoethyl)amino]carbonyl}phenyl)ethyl]piperidin-1-yl}carbonyl)oxy]nicotinate

Product 1

HCID 57507766Methyl 5-{[(4-{2-[3-(aziridin-1-ylcarbonyl)phenyl]ethyl}piperidin-1-yl)carbonyl]oxy}nicotinateYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A DMF (10 ml) suspension of methyl 5-[{(4-[2-(3-{[(2-bromoethyl)amino]carbonyl}phenyl)ethyl]piperidin-1-yl}carbonyl)oxy]nicotinate (750 mg), potassium carbonate (300 mg) and potassium iodide (361 mg) was stirred at 80° C. for 1 hour. The reaction liquid was left cooled, then EtOAc was added thereto, washed with aqueous saturated sodium hydrogencarbonate solution and saturated brine in that order, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1 (v/v)) to obtain methyl 5-{[(4-{2-[3-(aziridin-1-ylcarbonyl)phenyl]ethyl}piperidin-1-yl)carbonyl]oxy}nicotinate (630 mg) as a colorless oil.

Workup

  1. customThe reaction liquid
  2. waitwas left
  3. temperaturecooled
  4. washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1 (v/v))

Sources & evidence

ORD record
ord-ad1de77ada2e41d4827c98f47824c21c
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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