Diisopropylethylamine → N-(4-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzyl)-N-(4-fluorobenzyl)-6-(trifluoromethyl)pyridine-3-sulfonamide

HRID 1889669Notes

Reaction equation

HRID 1889669 reaction equation
[Cl:1][C:2]1[C:3]([OH:38])=[C:4]([S:9]([N:12]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:39][C:40]([F:52])([F:51])[C:41]1[N:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:3]([OH:38])=[C:4]([S:9]([N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[S:47]([C:44]3[CH:45]=[N:46][C:41]([C:40]([F:52])([F:39])[F:51])=[CH:42][CH:43]=3)(=[O:49])=[O:48])=[CH:16][CH:15]=2)[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 455943116-(Trifluoromethyl)pyridine-3-sulfonyl chlorideHCID 585314183,5-Dichloro-N-(4-fluorobenzyl)-N-(4-((4-fluorobenzylamino)methyl)benzyl)-2-hydroxybenzenesulfonamide

Product 1

HCID 86659763N-(4-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzyl)-N-(4-fluorobenzyl)-6-(trifluoromethyl)pyridine-3-sulfonamideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichloro-N-(4-fluorobenzyl)-N-(4-((4-fluorobenzylamino)methyl)benzyl)-2-hydroxybenzenesulfonamide (47 mg, 0.10 mmol) in CH2Cl2 (1 mL) were added 6-(trifluoromethyl)pyridine-3-sulfonyl chloride (25 mg, 0.10 mmol, Aldrich) and diisopropylethylamine (0.042 mL, 0.30 mmol). The reaction mixture was stirred at rt for 2 h, and then concentrated. The residue was dissolved in methanol and purified by prep HPLC to give the title compound (24.0 mg, 57%) as a white solid. 1H NMR (DMSO-d6) δ 11.17 (br s, 1H), 9.15 (s, 1H), 8.50 (d, 1H, J=8.1 Hz), 8.11 (d, 1H, J=8.1 Hz), 7.83 (d, 2H, J=2.3 Hz), 7.56 (d, 1H, J=2.3 Hz), 7.17-6.97 (m, 12H), 4.40 (s, 2H), 4.39 (s, 2H), 4.37 (s, 2H), 4.34 (s, 2H); MS (ESI): 786.1 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-1c714f6eaac64fc495f3ed1c519ede58
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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