Water → N-[2-(6-amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamide

HRID 1898224Notes

Reaction equation

HRID 1898224 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:15]([N:16](COC)[S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:14][C:13]([Cl:33])=[CH:12][N:11]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.O>Cl.O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:15]([NH:16][S:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:24][CH:25]=3)(=[O:18])=[O:19])=[CH:14][C:13]([Cl:33])=[CH:12][N:11]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 57942303N-[2-(6-Amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-N-methoxymethyl-benzenesulfonamide

Product 1

HCID 57942125N-[2-(6-amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamideYield 64%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-[2-(6-amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-N-methoxymethyl-benzenesulfonamide (58.6 mg, 1.03 mmol) in 4 N HCl in dioxane (4 mL) and water (1 mL) was stirred at 90° C. overnight. The reaction mixture was cooled to room temperature, evaporated to dryness, and treated with saturated aqueous NaHCO3 solution until pH 7-8. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4), and concentrated in vacuo. The obtained residue was purified via column chromatography (SiO2, 70% EtOAc in hexanes) to afford N-[2-(6-amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamide (34.5 mg) in 64% yield. 1H NMR (400 MHz, CDCl3) δ11.1 (s, 1H), 8.26 (d, 1H), 8.18 (d, 1H), 7.76 (d, 2H), 7.51 (t, 1H), 7.44 (d, 2H), 7.03 (d, 1H), 6.66 (d, 1H), 4.67 (s, 2H), 1.22 (s, 9H); ESMS m/z (relative intensity): 445.1 (M+H)+ (100).

Workup

  1. customevaporated to dryness
  2. additiontreated with saturated aqueous NaHCO3 solution until pH 7-8
  3. extractionThe mixture was extracted with EtOAc (2×25 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified via column chromatography (SiO2, 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f5da9b523ffb47d89478dc4b4546f7bd
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

Loading…