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Water → 3-Desmethyl Istradefylline

HRID 375368
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HRID 375368 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[OH:26])/[CH:5]=[CH:6]/[C:7]1[N:15]([CH3:16])[C:14]2[C:13](=[O:17])[N:12]([CH2:18][CH3:19])[C:11](=[O:20])[N:10]([CH2:21][CH3:22])[C:9]=2[N:8]=1.CI.[C:29](=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:18]([N:12]1[C:13](=[O:17])[C:14]2[N:15]([CH3:16])[C:7](/[CH:6]=[CH:5]/[C:4]3[CH:23]=[CH:24][C:25]([O:26][CH3:29])=[C:2]([OH:1])[CH:3]=3)=[N:8][C:9]=2[N:10]([CH2:21][CH3:22])[C:11]1=[O:20])[CH3:19]
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참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11125Lithium Carbonate2회HCID 1357703383,4-Didesmethyl Istradefylline

생성물 1

HCID 64489493-Desmethyl Istradefylline수율 76%

시약·촉매·용매 2

HCID 6212Chloroform용매
HCID 6228
Dimethylformamide
용매

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온도
80 °C

실험 절차

Compound 173 (400 mg, 1.12 mmol) obtained in Reference Example 112 was dissolved in 8 ml of dimethylformamide. To the solution were added 0.35 ml (5.62 mmol) of methyl iodide and 415 mg (5.62 mmol) of lithium carbonate, and the mixture was stirred at 80° C. for 3.5 hours. Water was added thereto to dissolve lithium carbonate, followed by addition of chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to give 127 mg (yield 76%) of Compound 174 as a pale brown powder. The obtained crude crystals were further recrystallized from ethanol.

후처리

  1. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customfollowed by evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

출처 및 근거

ORD 기록
ord-432ab3bebf994982a3e85d8e42a9e9fa
출처 데이터셋
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05484920

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