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

HRID 72651ノート

反応式

HRID 72651 の反応式
[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

参加物

4

反応物 2

HCID 6367Acetyl chlorideHCID 56598517HCID 56598517、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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,

後処理

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

出典と根拠

ORDレコード
ord-f3846ada55f74c94b1afed3965ed6eff
出典データセット
uspto-grants-2014_09
特許番号
US08829003B2

反応ノート

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