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

HRID 1438656Notes

Reaction equation

HRID 1438656 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) δ 11.1 (s, 1 H), 8.26 (d, 1 H), 8.18 (d, 1 H), 7.76 (d, 2H), 7.51 (t, 1 H), 7.44 (d, 2H), 7.03 (d, 1 H), 6.66 (d, 1 H), 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-8c87c9b9205c47f0af3ba39d2b45a3dc
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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