Potassium Carbonate → N-(4-(3,4-dimethoxyphenyl)-4-(1,3-dioxo-4-(4-((R)-1-phenylethyl)piperazin-1-yl)isoindolin-2-yl)butyl)thiophene-2-sulfonamide

HRID 42327

반응식

HRID 42327 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[N:26]2[CH2:31][CH2:30][N:29]([C@@H:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH3:33])[CH2:28][CH2:27]2)[C:17]1=[O:40])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[S:47]1[CH:51]=[CH:50][CH:49]=[C:48]1[S:52](Cl)(=[O:54])=[O:53]>ClCCl>[CH3:15][O:14][C:8]1[CH:7]=[C:6]([CH:5]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[N:26]3[CH2:31][CH2:30][N:29]([C@@H:32]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH3:33])[CH2:28][CH2:27]3)[C:17]2=[O:40])[CH2:4][CH2:3][CH2:2][NH:1][S:52]([C:48]2[S:47][CH:51]=[CH:50][CH:49]=2)(=[O:54])=[O:53])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 855182-Thiophenesulfonyl chlorideHCID 236272512-(4-amino-1-(3,4-dimethoxyphenyl)butyl)-4-(4-((R)-1-phenylethyl)piperazin-1-yl)isoindoline-1,3-dione

생성물 1

HCID 23627249N-(4-(3,4-dimethoxyphenyl)-4-(1,3-dioxo-4-(4-((R)-1-phenylethyl)piperazin-1-yl)isoindolin-2-yl)butyl)thiophene-2-sulfonamide수율 35.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A 10-mL round bottom flask was charge with Compound 66 (20.0 mg, 0.04 mmol), potassium carbonate (8.0 mg, 0.06 mmol), and dichloromethane (0.5 mL). Thiophene-2-sulfonyl chloride (8.0 mg, 0.04 mmol) was added and the mixture was stirred at room temperature for 4 h. The mixture was concentrated in vacuo and purified via flash chromatography (230-400 mesh silica gel 60, gradient 100:0-95:5 CH2Cl2:methanol) to give 9.8 mg of Compound 68 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.71-7.74 (m, 1 H), 7.51-7.61 (m, 3 H), 7.29-7.38 (m, 6 H), 7.02-7.18 (m, 3 H), 6.73-6.80 (m, 1 H), 5.10-5.17 (m, 1 H), 4.50-4.57 (m, 1 H), 3.86 (s, 3 H), 3.83 (s, 3 H), 3.31-3.39 (m, 4 H), 3.06-3.11 (m, 4 H), 2.65-2.74 (m, 2 H), 2.45-2.55 (m, 1 H), 2.20-2.31 (m, 1 H), 1.58-1.63 (m, 2 H), and 1.49 (d, J=6.8 Hz, 3 H); MS (ES+) 689 (M+1).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified via flash chromatography (230-400 mesh silica gel 60, gradient 100:0-95:5 CH2Cl2:methanol)

출처 및 근거

ORD 기록
ord-9b51dff94cc34a93b2ef0c6143a5a6c4
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536174B2

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