Triethylamine → 3-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzamide

HRID 1889662Notes

Reaction equation

HRID 1889662 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34]([Cl:36])[CH:35]=1)[CH2:5][N:6]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:7](=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:9]=1.[Cl:37][C:38]1[C:39]([OH:49])=[C:40]([S:45](Cl)(=[O:47])=[O:46])[CH:41]=[C:42]([Cl:44])[CH:43]=1.CCN(CC)CC>C1COCC1>[Cl:37][C:38]1[C:39]([OH:49])=[C:40]([S:45]([N:15]([CH2:14][C:10]2[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=2)[C:7]([N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:35]=[C:34]([Cl:36])[CH:33]=2)[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[O:24])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)(=[O:47])=[O:46])[CH:41]=[C:42]([Cl:44])[CH:43]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531676N-(3,5-Dichlorobenzyl)-N-(4-fluorobenzyl)-3-((4-fluorobenzylamino)methyl)benzamide

Product 1

HCID 585313833-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)-3-((4-fluorobenzylamino)methyl)benzamide (70 mg, 0.13 mmol) in THF (3 mL) were added 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (42 mg, 0.16 mmol) and Et3N (0.02 mL, 0.13 mmol). The resulting mixture was stirred at rt for 2 h, concentrated and the residue was dissolved in MeOH and purified by preparative HPLC to give the desired product as a white solid (51 mg, 51%). 1H NMR (CD3OD): δ 7.71 (s, 7.66 (d, J=4.0 Hz, 1H), 7.34-7.07 (m, 13H), 6.81 (t, J=8.0 Hz, 2H), 4.75-4.65 (m, 2H), 4.54 (s, 2H), 4.43-4.40 (m, 4H); MS (ESI): [M+H]+=751.0.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in MeOH
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c33a4ea903ea4b3b963a43a8743349e3
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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