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Triethylamine → 3,5-Dichloro-N-(3-(N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)sulfamoyl)benzyl)-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide

HRID 1889658
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HRID 1889658 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[C:35]([Cl:37])[CH:36]=1)[CH2:5][N:6]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:11]=1)(=[O:9])=[O:8].[Cl:38][C:39]1[C:40]([OH:50])=[C:41]([S:46](Cl)(=[O:48])=[O:47])[CH:42]=[C:43]([Cl:45])[CH:44]=1.CCN(CC)CC.S(Cl)(Cl)(=O)=O>C1COCC1>[Cl:38][C:39]1[C:40]([OH:50])=[C:41]([S:46]([N:17]([CH2:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([S:7](=[O:8])(=[O:9])[N:6]([CH2:5][C:4]3[CH:3]=[C:2]([Cl:1])[CH:36]=[C:35]([Cl:37])[CH:34]=3)[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:11]=2)[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)(=[O:48])=[O:47])[CH:42]=[C:43]([Cl:45])[CH:44]=1
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참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 24648Sulfuryl chlorideHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531573N-(3,5-Dichlorobenzyl)-N-(4-fluorobenzyl)-3-((4-fluorobenzylamino)methyl)benzenesulfonamide

생성물 1

HCID 585314823,5-Dichloro-N-(3-(N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)sulfamoyl)benzyl)-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide
수율 54.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)-3-((4-fluorobenzylamino)methyl)benzenesulfonamide (75 mg, 0.13 mmol) in THF (4 mL) at rt was added 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (38 mg, 0.15 mmol) and Et3N (0.06 mL, 0.40 mmol) and it was stirred at rt for 1.5 h. Additional sulfonyl chloride (15 mg) and Et3N (0.05 mL) were added to the reaction mixture, and it was continued to stir for 2 h. The mixture was concentrated and the residue was purified by preparative HPLC (Condition: solvent A: 10% MeOH-90% H2O-0.1% TFA; Solvent B: 90% MeOH-10% H2O-0.1% TFA. Column 3: YMC S5 ODS 20×100 mm; 45% B to final 100% B, gradient time: 10 minutes, flow rate: 20 ml/min) to give the desired product as a white solid (56 mg, 53%). 1H NMR (CD3OD): δ 7.72 (d, J=7.2 Hz, 1H), 7.70 (d, J=2.8 Hz, 1H), 7.64 (s, 1H), 7.58 (d, J=2.8 Hz, 1H), 7.50-7.46 (m, 2H), 7.20-7.10 (m, 5H), 6.93-6.90 (m, 6H), 4.61 (s, 2H), 4.46 (s, 2H), 4.26 (s, 2H), 4.21 (s, 21-1); MS (ESI): [M−H]−=784.9.

후처리

  1. stirringto stir for 2 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by preparative HPLC (Condition

출처 및 근거

ORD 기록
ord-2792361cb4814a2a9d84c251efe95463
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501992B2

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