Butane, 1,4-diisocyanato- → N,N'-(10,17-dioxo-3,6,21,24-tetraoxa-9,11,16,18-tetraazahexacosane-1,26-diyl)bis(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)

HRID 45763

Reaktionsgleichung

Reaktionsgleichung von HRID 45763
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]=[C:9]=[O:10])=[C:2]=[O:3].[NH2:11][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][C:27]([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:26][CH:25]=1)(=[O:23])=[O:22]>>[O:3]=[C:2]([NH:1][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:10])[NH: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:25]=[CH:26][C:27]([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:28][CH:29]=1)(=[O:23])=[O:22])[NH: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:25]=[CH:26][C:27]([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:28][CH:29]=1)(=[O:23])=[O:22]

Komponenten

3

Edukt 2

HCID 350453Butane, 1,4-diisocyanato-HCID 67458228N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2×

Produkt 1

HCID 86672373N,N'-(10,17-dioxo-3,6,21,24-tetraoxa-9,11,16,18-tetraazahexacosane-1,26-diyl)bis(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide)Ausbeute 3 %

Versuchsvorschrift

Compound 238 was prepared following the procedure outlined in Example 208 using 1,4-diisocyanatobutane (5.64 mg, 0.402 mmol) and N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (Compound 175.1, 58.8 mg, 0.805 mmol). Purification by preparative HPLC gave the title compound (13.8 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.86 (d, J=8 Hz, 2H), 7.72 (s, 2H), 7.61 (t, 2H), 7.52 (s, 2H), 7.47 (d, J=7 Hz, 2H), 7.18 (s, 5H), 7.78 (s, 2H), 4.77-4.68 (m, 5H), 4.48-4.40 (m, 2H), 3.35-3.28 (m, 2H), 3.56-3.51 (m, 16H), 3.45 (t, J=5 Hz, 5H), 3.35-3.32 (m, 10H), 3.09 (s, 6H), 3.03 (t, J=5 Hz, 3H). MS (m/z): 1145.01 [M+H]+.

Aufarbeitung

  1. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-459a7ab0c8554400bc4af5a9c54d0014
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541448B2

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