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

HRID 45759Notes

Reaction equation

HRID 45759 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][C:29]([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:28][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:29]1[CH:28]=[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:27]=[CH:28][C:29]([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:30][CH:31]=3)(=[O:25])=[O:24])=[O:12])=[CH:10][CH:9]=2)(=[O:25])=[O:24])=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 7489Terephthalic AcidHCID 67458228N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2×

Product 1

HCID 86672370N1,N4-bis(2-(2-(2-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethyl)terephthalamideYield 12.7%

Procedure

Compound 231 was prepared following the procedure outlined in Example 215 using terephthalic acid (11.4 mg, 0.0684 mmol) and 4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-N-(2-(2-(2-hydroxyethoxy)ethoxy)-ethyl)benzenesulfonamide (Compound 175.1, 100 mg, 0.136 mmol). Purification by preparative HPLC gave the title compound (9.8 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.86-7.85 (m, 9H), 7.83 (s, 2H), 7.50 (s, 1H), 7.41 (d, 4H), 6.80 (s, 1H), 3.68-3.42 (m, 26H), 3.34 (m, 2H), 3.09-3.01 (m, 12H). MS (m/z): 1135.07 [M+H]+.

Workup

  1. customCompound 231 was prepared
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-df1344e0b695464b93e50536e3bdf667
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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