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异氰酸苯酯 → 5'-Phenylaminocarbonylaminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 841069
笔记
打印预览

反应方程式

HRID 841069 反应方程式
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:12]=[C:13]2[CH2:19][C:18]3([CH:24]4[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]4)[CH2:20]3)[O:17][C:14]2=[N:15][CH:16]=1>O1CCCC1>[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:12]=[C:13]3[CH2:19][C:18]4([CH:24]5[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]5)[CH2:20]4)[O:17][C:14]3=[N:15][CH:16]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参与物实验过程后处理来源与证据反应笔记

参与物

4

反应物 2

HCID 7672异氰酸苯酯HCID 15908236spiro[1-azabicyclo[2.2.2]octane-3,2'-3H-furo[2,3-b]pyridine]-5'-amine

产物 1

HCID 100207835'-Phenylaminocarbonylaminospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]收率 86%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

Under a nitrogen atmosphere, phenyl isocyanate (0.056 mL, 0.515 mmol) was added to a suspension of 5′-aminospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (119 mg, 0.514 mmol) in anhydrous tetrahydrofuran (5 mL) and stirred for 12 hours. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography through silica gel, eluting with ammoniated chloroform/methanol (92.5:7.5), to obtain the title compound (155 mg, 0.442 mmol, 86%) as an off-white solid: electrospray MS (m/z, relative intensity) 351 ([MH]+, 100).

后处理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue purified by flash chromatography through silica gel
  3. washeluting with ammoniated chloroform/methanol (92.5:7.5)

来源与证据

ORD记录
ord-1b0d805b21b74e9aa171f5144eac8298
来源数据集
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
专利号
US06369224B1

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记