3,5-Dichloro-2-hydroxybenzenesulphonyl chloride → Methyl 6-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)-methyl)picolinate

HRID 1889724Notes

Reaction equation

HRID 1889724 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[C:23]([OH:33])=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[C:26]([Cl:28])[CH:27]=1>C1COCC1>[Cl:21][C:22]1[C:23]([OH:33])=[C:24]([S:29]([N:7]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=2)(=[O:31])=[O:30])[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

4

Reactant 2

HCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 58531465Methyl 6-(((4-fluorobenzyl)amino)methyl)picolinate

Product 1

HCID 58531362Methyl 6-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)-methyl)picolinateYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-((4-fluorobenzylamino)methyl)picolinate (140 mg, 0.51 mmol) in THF (3 mL) were added 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (147 mg, 0.56 mmol) and TEA (0.142 mL, 1.02 mmol). The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing the desired product were combined, concentrated and lyophilized to give the desired product (0.19 g, 74%) as a white solid. 1H NMR (CD3OD) δ 7.93-7.80 (m, 2H), 7.65-7.53 (m, 3H), 7.27-7.25 (m, 2H), 6.94-6.90 (m, 2H), 4.68 (s, 2H), 4.65 (s, 2H), 3.98 (s, 3H). MS (ESI): 499.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC
  3. additionFractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebd99435d65740d2be33ac0712be262a
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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