N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide → N1,N3-bis(2-(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,2-dimethylmalonamide

HRID 45734

반응식

HRID 45734 반응식
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]2[C:32]3[C:27](=[C:28]([Cl:34])[CH:29]=[C:30]([Cl:33])[CH:31]=3)[CH2:26][N:25]([CH3:35])[CH2:24]2)[CH:18]=1)(=[O:16])=[O:15].[CH3:36][C:37]([CH3:58])([C:48]([O:50]N1C(=O)CCC1=O)=O)[C:38]([O:40]N1C(=O)CCC1=O)=O>>[Cl:33][C:30]1[CH:31]=[C:32]2[C:27](=[C:28]([Cl:34])[CH:29]=1)[CH2:26][N:25]([CH3:35])[CH2:24][CH:23]2[C:19]1[CH:18]=[C:17]([S:14]([NH:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:48](=[O:50])[C:37]([CH3:36])([CH3:58])[C:38]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]3[C:32]4[C:27](=[C:28]([Cl:34])[CH:29]=[C:30]([Cl:33])[CH:31]=4)[CH2:26][N:25]([CH3:35])[CH2:24]3)[CH:18]=2)(=[O:16])=[O:15])=[O:40])(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=1

참가 물질

3

반응물 2

HCID 67458308N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamideHCID 86672351Bis(2,5-dioxopyrrolidin-1-yl) 2,2-dimethylmalonate

생성물 1

HCID 86672350N1,N3-bis(2-(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,2-dimethylmalonamide

실험 절차

Compound 182 was prepared from compound 28 and bis(2,5-dioxopyrrolidin-1-yl) 2,2-dimethylmalonate (prepared using the methods outlined in example 168) following the procedure outlined in example 175. The crude product (250 mg) was purified by Prep-HPLC with the following conditions: Column, C18 silica gel; mobile phase, MeCN/H2O/CF3COOH=39/100/0.05; Detector, UV 254 nm. This resulted in 152.3 mg (47%) of a TFA salt of N1,N3-bis(2-(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,2-dimethylmalonamide as a white solid. 1H-NMR (300 MHz, CDCl3, ppm): δ 7.92-7.89 (d, J=8.1 Hz, 2H), 7.79 (s, 2H), 7.69˜7.64 (m, 2H), 7.57-7.55 (d, J=7.5 Hz, 4H), 3.68 (s, 2H), 4.87-4.75 (m, 4H), 4.54˜4.49 (m, 2H), 3.90-3.88 (m, 2H), 3.67-3.45 (m, 20H), 3.39-3.32 (m, 4H), 3.31 (s, 6H), 3.17-3.05 (m, 4H), 1.41 (s, 1H). MS (m/z): 1189 [M+H]+.

후처리

  1. customprepared
  2. customThe crude product (250 mg) was purified by Prep-HPLC with the following conditions

출처 및 근거

ORD 기록
ord-7a7c3fa586b14e17a3f396af2b0f46bf
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541448B2

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