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

Reaction equation

HRID 45745 reaction equation
[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]

Participants

6

Reactant 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×

Product 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)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  1. customthe reaction was purified by preparative HPLC

Sources & evidence

ORD record
ord-582581cc492a4d04acc73a7c07708fa1
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

Loading…