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

HRID 72652ノート

反応式

HRID 72652 の反応式
[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

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 56598517HCID 56598517、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-40881723a56f492ab09c65e77d4acce6
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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