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Water → 3-Desmethyl Istradefylline

HRID 1081844
ノート
印刷プレビュー

反応式

HRID 1081844 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11125Lithium Carbonate2 回HCID 1357703383,4-Didesmethyl Istradefylline

生成物 1

HCID 64489493-Desmethyl Istradefylline収率 76%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2b5b4050f4f14bfd96039e6b449c5bfb
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05587378

反応ノート

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