Terephthalic Acid → N1,N4-bis(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethyl)terephthalamide

HRID 45761

Reaction equation

HRID 45761 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]2[C:41]3[C:36](=[C:37]([Cl:43])[CH:38]=[C:39]([Cl:42])[CH:40]=3)[CH2:35][N:34]([CH3:44])[CH2:33]2)[CH:27]=1)(=[O:25])=[O:24]>>[Cl:42][C:39]1[CH:40]=[C:41]2[C:36](=[C:37]([Cl:43])[CH:38]=1)[CH2:35][N:34]([CH3:44])[CH2:33][CH:32]2[C:28]1[CH:27]=[C:26]([S:23]([NH:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][NH:13][C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([C:1]([NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]4[C:41]5[C:36](=[C:37]([Cl:43])[CH:38]=[C:39]([Cl:42])[CH:40]=5)[CH2:35][N:34]([CH3:44])[CH2:33]4)[CH:27]=3)(=[O:25])=[O:24])=[O:12])=[CH:10][CH:9]=2)(=[O:25])=[O:24])[CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 7489Terephthalic AcidHCID 67458027N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2×

Product 1

HCID 86672372N1,N4-bis(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethyl)terephthalamideYield 63.5%

Procedure

Compound 234 was prepared following the procedures outlined in Example 215 using terephthalic acid (13.8 mg, 0.0833 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, 121.7 mg, 0.167 mmol). Purification by preparative HPLC gave the title compound (60.0 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.88 (m, 6H), 7.72 (s, 2H), 7.61 (t, 2H), 7.51 (m, 4H), 6.80 (s, 2H), 4.88-4.75 (m, 4H), 4.75 (d, 2H), 4.74 (m, 2H), 3.85-3.42 (m, 25H), 3.12 (s, 6H), 2.99 (t, 4H). MS (m/z): 1135.11 [M+H]+.

Workup

  1. customCompound 234 was prepared
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-d0783cb48fac4a928f95d82f3691c701
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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