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4-Methylmorpholine → 3-(4-Chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentyl methanesulfonate

HRID 1427295
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HRID 1427295 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:14]2[C:22]3[C:17](=[C:18]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)([CH2:12][CH3:13])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.CN1CCOCC1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:35][S:36]([O:11][CH2:10][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([N:14]1[C:22]2[C:17](=[C:18]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1)[CH2:12][CH3:13])(=[O:38])=[O:37]
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참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 70560533N-(1-(3-(4-Chlorophenyl)-1-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide

생성물 1

HCID 867050593-(4-Chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentyl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of N-(1-(3-(4-chlorophenyl)-1-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide (20 mg, 0.05 mmol), as described in Example 40 Step I, and NMM (10 mg, 0.1 mmol) in DCM (3 mL) was added methanesulfonyl chloride (7 mg, 0.06 mmol). Then the mixture was stirred at room temperature for 1 h, quenched with saturated ammonium chloride solution (5 mL), and extracted with ethyl acetate. The organic layers were washed with brine (5 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by Prep-TLC (PE/EA=4/1) to afford the title compound as colorless oil. LC/MS m/z=485.1[M+H]+.

후처리

  1. customquenched with saturated ammonium chloride solution (5 mL)
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine (5 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by Prep-TLC (PE/EA=4/1)

출처 및 근거

ORD 기록
ord-c5214852562b411a847a8d0b4d5e0f29
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933113B2

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