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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
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HRID 1787002 반응식
[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
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참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-80d75f639085448fa4e4b23a2c3e8e72
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07507740B2

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