Methanesulfonyl chloride → (E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)methanesulfonamide

HRID 72652Notes

Reaction equation

HRID 72652 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[C:13]([NH2:14])=[CH:12][C:11]([CH2:15][S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])(=[O:18])=[O:17])=[CH:10][N:9]=1>N1C=CC=CC=1>[CH3:6][O:7][C:8]1[C:13]([NH:14][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:12][C:11]([CH2:15][S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])(=[O:18])=[O:17])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 56598517HCID 56598517, compound

Product 1

HCID 54759259(E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)methanesulfonamideYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.048 mL, 0.31 mmol) was added dropwise into the solution of (E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-amine (111 mg, 0.28 mmol) in dry pyridine (7 mL) on an ice bath. After warming up to room temperature the mixture was stirred overnight. After evaporated to dryness, the residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:2 v/v) to afford pure product as a white solid (42 mg, 32%) 1H-NMR (Acetone-do): δ 2.98 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 3.93 (s, 6H, 2×OCH3), 3.97 (s, 3H, OCH3), 4.38 (s, 2H, CH2), 6.31 (s, 2H, Ph-H), 7.19 (d, 1H, J=15.6 Hz, CH), 7.71 (d, 1H, J=15.6 Hz, CH), 7.85 (d, 1H, J=2.0 Hz, Py-H), 7.97 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (Acetone-d6): δ 38.78, 53.30, 55.08, 55.53, 57.36, 90.67, 103.24, 119.44, 121.70, 123.17, 130.21, 134.70, 143.67, 154.11, 161.54, 164.28; HR-MS (ESI+) m/z 473.1115 [M+H]+ C19H24N2O832 requires 472.0974.

Workup

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

Sources & evidence

ORD record
ord-40881723a56f492ab09c65e77d4acce6
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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