Methanesulfonyl chloride → HCID 86276169, compound

HRID 72664Notes

Reaction equation

HRID 72664 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:27])=[N:5][C:6]([CH2:9][S:10](/[CH:13]=[CH:14]/[C:15]2[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=2[O:25][CH3:26])(=[O:12])=[O:11])=[CH:7][CH:8]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([NH:27][S:29]([CH3:28])(=[O:31])=[O:30])=[N:5][C:6]([CH2:9][S:10](/[CH:13]=[CH:14]/[C:15]2[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=2[O:25][CH3:26])(=[O:11])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86276168HCID 86276168, compound

Product 1

HCID 86276169HCID 86276169, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of (E)-3-methoxy-6-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-2-amine (333 mg, 0.84 mmol) in dry pyridine (20 mL) cooling on an ice bath methanesulfonyl chloride (0.3 mL, 2 mmol) was added dropwise. The mixture was stirred at room temperature for 20 hours. After evaporated to dryness, the residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:1 v/v) to afford 20 mg of the title compound as white powder. 1H-NMR (DMSO-d6): δ 3.26 (s, 3H, OCH3), 3.82 (s, 3H, CH3), 3.85 (s, 9H, 3×OCH3), 4.45 (s, 2H, CH2), 6.30 (s, 2H, Ph-H), 7.14 (d, 1H, J=15.6 Hz, CH), 7.15 (d, 1H, J=8.8 Hz, Py-H), 7.41 (d, 1H, J=8.4 Hz, Py-H), 7.56 (d, 1H, J=15.6 Hz, CH), 9.73 (s, 1H, NH).

Workup

  1. additionwas added dropwise
  2. customAfter evaporated to dryness
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with PE/EtOAc (1:1 v/v)

Sources & evidence

ORD record
ord-480af4abb772489f8a9797461de2bff3
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

Loading…