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

HRID 2074311
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HRID 2074311 반응식
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
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6

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

생성물 1

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

시약·촉매·용매

1
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-9155d0f775864eed83a8b37116d52a40
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07919495B2

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