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

HRID 45750

反応式

HRID 45750 の反応式
[OH:1][C@H:2]([C@@H: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][NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]2[C:53]3[C:48](=[C:49]([Cl:55])[CH:50]=[C:51]([Cl:54])[CH:52]=3)[CH2:47][N:46]([CH3:56])[CH2:45]2)[CH:39]=1)(=[O:37])=[O:36]>>[Cl:54][C:51]1[CH:52]=[C:53]2[C:48](=[C:49]([Cl:55])[CH:50]=1)[CH2:47][N:46]([CH3:56])[CH2:45][CH:44]2[C:40]1[CH:39]=[C:38]([S:35]([NH:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][NH:25][C:3](=[O:5])[C@H:2]([OH:1])[C@@H:13]([OH:24])[C:14]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]3[C:53]4[C:48](=[C:49]([Cl:55])[CH:50]=[C:51]([Cl:54])[CH:52]=4)[CH2:47][N:46]([CH3:56])[CH2:45]3)[CH:39]=2)(=[O:37])=[O:36])=[O:16])(=[O:37])=[O:36])[CH:43]=[CH:42][CH:41]=1

参加物

3

反応物 2

HCID 124912Disuccinimidyl tartarateHCID 67458027N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2 回

生成物 1

HCID 86699386(2R,3R)-N1,N4-bis(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethyl)-2,3-dihydroxysuccinamide収率 15.3%

実験手順

Compound 218 was prepared following the procedure outlined in Example 168 using (2R,3R)-bis(2,5-dioxopyrrolidin-1-yl) 2,3-dihydroxysuccinate (10.2 mg, 0.0298 mmol) and N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (Compound 168.2, 30 mg, 0.0597 mmol). Purification by preparative HPLC gave the title compound (5.1 mg) as the TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.92 (d, J=7.8 Hz, 2H), 7.82 (m, 2H), 7.67 (t, J=7.8 Hz, 2H), 7.57 (m, 2H), 7.55 (d, J=6.9 Hz, 2H), 6.86 (m, 2H), 4.84 (s, 2H), 4.79 (s, 2H), 4.54 (d, 2H), 4.48 (s, 2H), 3.92 (m, 2H), 3.53 (m, 22H), 3.18 (s, 6H), 3.07 (t, J=5.4 Hz, 4H). MS (m/z): 1119.04 [M+H]+.

後処理

  1. customCompound 218 was prepared
  2. customPurification by preparative HPLC

出典と根拠

ORDレコード
ord-699248c3535f49e8a989e00134e1af77
出典データセット
uspto-grants-2013_09
特許番号
US08541448B2

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