Disuccinimidyl tartrate → N1,N4-bis(2-(2-(2-(2-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,3-dihydroxysuccinamide

HRID 45755

反応式

HRID 45755 の反応式
[OH:1][CH:2]([CH:13]([OH:24])[C:14]([O:16]N1C(=O)CCC1=O)=O)[C:3]([O:5]N1C(=O)CCC1=O)=O.[NH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][NH:37][S:38]([C:41]1[CH:46]=[CH:45][C:44]([CH:47]2[C:56]3[C:51](=[C:52]([Cl:58])[CH:53]=[C:54]([Cl:57])[CH:55]=3)[CH2:50][N:49]([CH3:59])[CH2:48]2)=[CH:43][CH:42]=1)(=[O:40])=[O:39]>>[Cl:57][C:54]1[CH:55]=[C:56]2[C:51](=[C:52]([Cl:58])[CH:53]=1)[CH2:50][N:49]([CH3:59])[CH2:48][CH:47]2[C:44]1[CH:43]=[CH:42][C:41]([S:38]([NH:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][NH:25][C:3](=[O:5])[CH:2]([OH:1])[CH:13]([OH:24])[C:14]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][NH:37][S:38]([C:41]2[CH:42]=[CH:43][C:44]([CH:47]3[C:56]4[C:51](=[C:52]([Cl:58])[CH:53]=[C:54]([Cl:57])[CH:55]=4)[CH2:50][N:49]([CH3:59])[CH2:48]3)=[CH:45][CH:46]=2)(=[O:40])=[O:39])=[O:16])(=[O:40])=[O:39])=[CH:46][CH:45]=1

参加物

3

反応物 2

HCID 334527Disuccinimidyl tartrateHCID 46843244N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2 回

生成物 1

HCID 86672367N1,N4-bis(2-(2-(2-(2-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,3-dihydroxysuccinamide収率 19.8%

実験手順

Compound 227 was prepared following the procedure outlined in Example 168 using bis(2,5-dioxopyrrolidin-1-yl) 2,3-dihydroxysuccinate (49.6 mg, 0.144 mmol) and N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (Compound 82, 157 mg, 0.288 mmol). Purification by preparative HPLC gave the title compound (34.5 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.89 (d, 4H), 7.53 (s, 2H), 7.45 (d, 4H), 6.83 (s, 2H), 4.77-4.74 (m, 6H), 4.46 (d, 2H), 4.43 (t, 2H), 3.89-3.84 (m, 2H), 3.62-3.53 (m, 19H), 3.49-3.41 (m, 13H), 3.14 (s, 6H), 3.08 (t, 4H). MS (m/z): 1206.94 [M+H]+.

後処理

  1. customCompound 227 was prepared
  2. customPurification by preparative HPLC

出典と根拠

ORDレコード
ord-67e767d445104f2e974da8459d5d7c64
出典データセット
uspto-grants-2013_09
特許番号
US08541448B2

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