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

HRID 72651노트

반응식

HRID 72651 반응식
[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

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 56598517HCID 56598517, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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,

후처리

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

출처 및 근거

ORD 기록
ord-f3846ada55f74c94b1afed3965ed6eff
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829003B2

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