2-Chloropyridine-3-sulfonyl chloride → 2-Chloro-N-(5,6-dimethoxypyridin-3-yl)pyridine-3-sulfonamide

HRID 1772934Notes

Reaction equation

HRID 1772934 reaction equation
[Cl:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH2:22])[CH:17]=[N:18][C:19]=1[O:20][CH3:21].Cl[C:24]1[C:29]([S:30](NC2C=CC(OC)=C(OC)N=2)(=[O:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1>N1C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[C:7]([S:8]([NH:22][C:16]2[CH:17]=[N:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:3][C:24]1[C:29]([S:30]([NH:22][C:16]2[CH:17]=[N:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)(=[O:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

7

Reactant 3

HCID 102199682-Chloropyridine-3-sulfonyl chlorideHCID 127582145,6-Dimethoxypyridin-3-amineHCID 900227962-Chloro-N-(5,6-dimethoxypyridin-2-yl)pyridine-3-sulfonamide

Product 2

HCID 900214752-Chloro-N-(5,6-dimethoxypyridin-3-yl)pyridine-3-sulfonamideHCID 900305322-amino-N-(5,6-dimethoxypyridin-3-yl) pyridine-3-sulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-N-(5,6-dimethoxypyridin-3-yl)pyridine-3-sulfonamide (20.0 g, 60.7 mmol) was prepared from 2-chloropyridine-3-sulfonyl chloride (13.7 g, 64.9 mmol) and 5,6-dimethoxypyridin-3-amine (10 g, 64.9 mmol) in pyridine (50 mL) at rt using the methods of (IntC1), step 1. 2-Chloro-N-(5,6-dimethoxypyridin-2-yl)pyridine-3-sulfonamide (3.0 g, 9.09 mmol) was dissolved in THF (20 mL) and NH3(g) bubbled through the reaction mixture at −40° C. for 15 min. The reaction mixture was stirred for 1 d at rt before concentration in vacuo. Purification by column chromatography eluting with 50-60% EtOAc in hexane yielded the title compound (2.0 g, 6.44 mmol) as a white solid.

Workup

  1. customNH3(g) bubbled through the reaction mixture at −40° C. for 15 min
  2. customPurification by column chromatography
  3. washeluting with 50-60% EtOAc in hexane

Sources & evidence

ORD record
ord-4ebc8d45b59f43df82f7039d7023bd36
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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