Triethylamine → N-(3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl)-N-isobutylpyridine-3-sulfonamide

HRID 1889642Notes

Reaction equation

HRID 1889642 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[Cl:11][C:12]1[C:13]([OH:41])=[C:14]([S:19]([N:22]([CH2:27][C:28]2[CH:33]=[C:32]([CH2:34][NH:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH:31]=[C:30]([Cl:40])[CH:29]=2)[CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:21])=[O:20])[CH:15]=[C:16]([Cl:18])[CH:17]=1.CCN(CC)CC>C1COCC1>[Cl:40][C:30]1[CH:31]=[C:32]([CH:33]=[C:28]([CH2:27][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:19]([C:14]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:12]([Cl:11])[C:13]=2[OH:41])(=[O:21])=[O:20])[CH:29]=1)[CH2:34][N:35]([CH2:36][CH:37]([CH3:39])[CH3:38])[S:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 585315243,5-Dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamide

Product 1

HCID 44594685N-(3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl)-N-isobutylpyridine-3-sulfonamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyridine-3-sulfonyl chloride (70 mg, 0.40 mmol) in THF (4 mL) were added 3,5-dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamide (100 mg, 0.20 mmol) and Et3N (0.14 mL, 0.98 mmol). The reaction mixture was stirred at rt for 3 h. The mixture was concentrated. To the residue was added 1 N NaOH/THF/MeOH. After 4 h, the mixture was concentrated and the residue was purified by preparative HPLC. Fractions containing the desired product were combined, concentrated, and lyophilized to give the desired product as a white solid (60 mg, 40%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionTo the residue was added 1 N NaOH/THF/MeOH
  3. waitAfter 4 h
  4. concentrationthe mixture was concentrated
  5. customthe residue was purified by preparative HPLC
  6. additionFractions containing the desired product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-62de9c1deb8644b28967deab78389598
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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