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m-Chloroperbenzoic acid → 2-[(2-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5h-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethyl)sulfinyl]ethanol

HRID 1787002
ノート
印刷プレビュー

反応式

HRID 1787002 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][O:31]CCO)[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[OH:35][CH2:36][CH2:37][S-:38].[Na+].Cl[C:41]1C=CC=C(C(OO)=O)[CH:42]=1.C(=O)([O-])[OH:52].[Na+]>ClCCl.CN(C)C=O.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][O:31][CH2:41][CH2:42][S:38]([CH2:37][CH2:36][OH:35])=[O:52])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 116846292-(2-(4-((3-chloro-4-(3-(trifluoromethyl)phenoxy)phenyl)amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy)ethan-1-olHCID 23668038Sodium 2-hydroxyethanethiolate

生成物 1

HCID 575971532-[(2-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5h-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethyl)sulfinyl]ethanol

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The compound (120 mg) obtained by the reaction in the same manner as in Example 172 (i) using the compound (200 mg) of Example 147, sodium 2-hydroxyethanethiolate (2.02 g), tetrahydrofuran (6.0 mL) and N,N-dimethylformamide (5.0 mL) was dissolved in dichloromethane (7.0 mL). m-Chloroperbenzoic acid (110 mg) was added at −18° C. and the mixture was stirred for 5 hrs. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate and concentrated, and the residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=80:20). Crystallization from diethyl ether/ethyl acetate/hexane gave the title compound (97.0 mg).

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue was separated
  6. custompurified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=80:20)
  7. customCrystallization from diethyl ether/ethyl acetate/hexane

出典と根拠

ORDレコード
ord-80d75f639085448fa4e4b23a2c3e8e72
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07507740B2

反応ノート

読み込み中…

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