D-Tartaric acid → (2S,3S)-N1,N4-bis(2-(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,3-dihydroxysuccinamide

HRID 45754

Reaction equation

HRID 45754 reaction equation
[OH:1][C@@H:2]([C@H:6]([OH:10])[C:7]([OH:9])=O)[C:3]([OH:5])=O.[NH2:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]2[C:42]3[C:37](=[C:38]([Cl:44])[CH:39]=[C:40]([Cl:43])[CH:41]=3)[CH2:36][N:35]([CH3:45])[CH2:34]2)[CH:28]=1)(=[O:26])=[O:25]>>[Cl:43][C:40]1[CH:41]=[C:42]2[C:37](=[C:38]([Cl:44])[CH:39]=1)[CH2:36][N:35]([CH3:45])[CH2:34][CH:33]2[C:29]1[CH:28]=[C:27]([S:24]([NH:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][NH:11][C:3](=[O:5])[C@@H:2]([OH:1])[C@H:6]([OH:10])[C:7]([NH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]3[C:42]4[C:37](=[C:38]([Cl:44])[CH:39]=[C:40]([Cl:43])[CH:41]=4)[CH2:36][N:35]([CH3:45])[CH2:34]3)[CH:28]=2)(=[O:26])=[O:25])=[O:9])(=[O:26])=[O:25])[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 439655D-Tartaric acidHCID 67458308N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2×

Product 1

HCID 86672366(2S,3S)-N1,N4-bis(2-(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)-2,3-dihydroxysuccinamideYield 32.1%

Procedure

Compound 222 was prepared following the procedure outlined in Example 215 using (2S,3S)-2,3-dihydroxysuccinic acid (15.5 mg, 0.103 mmol) and N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (Compound 28, 112 mg, 0.206 mmol). Purification by preparative HPLC gave the title compound (39.9 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.87 (d, 2H), 7.77 (s, 2H), 7.63 (t, 2H), 7.54-7.50 (m, 4H), 6.82 (s, 2H), 4.34 (s, 2H), 3.90-3.85 (m, 1H), 3.62-3.30 (m, 47H), 3.14 (m, 8H), 3.05 (t, 4H). MS (m/z): 1206.95 [M+H]+.

Workup

  1. customCompound 222 was prepared
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-bc39819a3f4442eba2249eab4ca9cdfd
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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