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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
ノート
印刷プレビュー

反応式

HRID 1889658 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 24648Sulfuryl chlorideHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531573N-(3,5-Dichlorobenzyl)-N-(4-fluorobenzyl)-3-((4-fluorobenzylamino)methyl)benzenesulfonamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2792361cb4814a2a9d84c251efe95463
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08501992B2

反応ノート

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