Trifluoroacetic acid → N,N'-(13,20-dioxo-3,6,9,24,27,30-hexaoxa-12,14,19,21-tetraazadotriacontane-1,32-diyl)bis(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)

HRID 45745

Reaktionsgleichung

Reaktionsgleichung von HRID 45745
[C:1]([OH:7])([C:3](F)(F)F)=O.[NH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]2[C:39]3[C:34](=[C:35]([Cl:41])[CH:36]=[C:37]([Cl:40])[CH:38]=3)[CH2:33][N:32]([CH3:42])[CH2:31]2)[CH:25]=1)(=[O:23])=[O:22].[N:43]([CH2:46][CH2:47][CH2:48][CH2:49][N:50]=[C:51]=[O:52])=[C:44]=[O:45].[CH:53]([N:56]([CH:59]([CH3:61])C)[CH2:57][CH3:58])(C)C>CN(C=O)C>[O:45]=[C:44]([NH:43][CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51](=[O:52])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:7][CH2:1][CH2:3][NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:61]2[C:39]3[C:58](=[C:35]([Cl:41])[CH:36]=[C:37]([Cl:40])[CH:38]=3)[CH2:57][N:56]([CH3:53])[CH2:59]2)[CH:25]=1)(=[O:22])=[O:23])[NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]2[C:39]3[C:34](=[C:35]([Cl:41])[CH:36]=[C:37]([Cl:40])[CH:38]=3)[CH2:33][N:32]([CH3:42])[CH2:31]2)[CH:25]=1)(=[O:23])=[O:22]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 350453Butane, 1,4-diisocyanato-HCID 67458308N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2×

Produkt 1

HCID 86672360N,N'-(13,20-dioxo-3,6,9,24,27,30-hexaoxa-12,14,19,21-tetraazadotriacontane-1,32-diyl)bis(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of a TFA salt of 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) (47 mg, 0.061 mmol) in DMF (0.20 mL) was added 1,4-diisocyanatobutane (4.0 mg, 0.03 mmol) followed by diisopropylethylamine (15 mg, 0.12 mmol). After stirring at room temperature for 30 minutes, the reaction was purified by preparative HPLC to give the title compound (31 mg) as a TFA salt. 1H-NMR (400 mHz, CD3OD) δ 7.88 (m, 2H), 7.75 (m, 2H), 7.63 (m, 2H), 7.54 (m, 4H), 6.83 (m, 2H), 4.74 (m, 4H), 4.48 (m, 2H), 3.87 (m, 2H), 3.62-3.55 (m, 14H), 3.51-3.43 (m, 12H), 3.24 (m, 4H), 3.14 (s, 6H), 3.05 (m, 8H), 1.43 (m, 4H). MS (m/z): 1230.99 [M+H]+.

Aufarbeitung

  1. customthe reaction was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-582581cc492a4d04acc73a7c07708fa1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541448B2

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