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

HRID 72651Notes

Reaction equation

HRID 72651 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[C:12]([NH2:13])=[CH:11][C:10]([CH2:14][S:15](/[CH:18]=[CH:19]/[C:20]2[C:25]([O:26][CH3:27])=[CH:24][C:23]([O:28][CH3:29])=[CH:22][C:21]=2[O:30][CH3:31])(=[O:17])=[O:16])=[CH:9][N:8]=1>N1C=CC=CC=1>[CH3:5][O:6][C:7]1[C:12]([NH:13][C:1](=[O:3])[CH3:2])=[CH:11][C:10]([CH2:14][S:15](/[CH:18]=[CH:19]/[C:20]2[C:25]([O:26][CH3:27])=[CH:24][C:23]([O:28][CH3:29])=[CH:22][C:21]=2[O:30][CH3:31])(=[O:17])=[O:16])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 56598517HCID 56598517, compound

Product 1

HCID 86690903(E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)acetamideYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (0.054 mL, 0.76 mmol) was added dropwise into the solution of (E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-amine (80 mg, 0.21 mmol) in dry pyridine (5 mL) on an ice bath. The mixture was warmed to room temperature and stirred overnight. After evaporated to dryness, the residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:3 v/v) to afford pure product as a white solid (38 mg, 44%). 1H-NMR (CDCl3-d6): δ 2.21 (s, 3H, CH3), 3.86 (s, 6H, 2×OCH3), 3.87 (s, 3H, OCH3), 4.03 (s, 3H, OCH3), 4.21 (s, 2H, CH2), 6.11 (s, 2H, Ph-H), 7.13 (d, 1H, J=15.6 Hz, CH), 7.61 (s, 1H, NH), 7.88 (d, 1H, J=15.6 Hz, CH), 7.89 (d, 1H, J=2.0 Hz, Py-H), 8.65 (d, 1H, J=2.0 Hz, Py-H); HR-MS (ESI+) m/z 437.1460 [M+H]+ C20H24N2O7S requires 436.1304,

Workup

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

Sources & evidence

ORD record
ord-f3846ada55f74c94b1afed3965ed6eff
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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