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三乙胺 → 3-Methoxy-N-(2-methyl-thiazol-4-ylmethoxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 1663155
笔记
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反应方程式

HRID 1663155 反应方程式
[CH3:1][O:2][C:3]1[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.C(N(CC)CC)C.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.Cl.[CH3:50][C:51]1[S:52][CH:53]=[C:54]([CH2:56][O:57][NH2:58])[N:55]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:58][O:57][CH2:56][C:54]1[N:55]=[C:51]([CH3:50])[S:52][CH:53]=1)=[O:8]
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

7

反应物 4

HCID 8471三乙胺HCID 27332072-(1H-苯并三偶氮L-1-基)-1,1,3,3-四甲基脲四氟硼酸酯HCID 54606663HCID 54606663,化合物HCID 589898483-Methoxy-2-[(pyridin-4-ylmethyl)-amino]-benzoic acid

产物 1

HCID 112228443-Methoxy-N-(2-methyl-thiazol-4-ylmethoxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

试剂、催化剂与溶剂 2

HCID 962
聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]
溶剂
HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
90 °C

实验过程

3-Methoxy-2-[(pyridin-4-ylmethyl)-amino]-benzoic acid (200 mg, see preparation 1D) was dissolved in DMF (20 ml) and triethylamine (0.65 ml) at 50-60° C. N,N,N′,N′-Tetramethyl-O-(benzotriazole-1-yl)uronium-tetrafluoroborate (250 mg) was added and after 5 minutes O-(2-methyl-thiazol-4-ylmethyl)-hydroxylamine hydrochloride (209 mg, see preparation 12) was added. The reaction mixture was heated to 90° C. and stirred at this temperature for 2 hours. The mixture was cooled to room temperature and water was added. The mixture was extracted several times with EtOAc and the combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The remaining material was purified by column chromatography on silica gel (elution with 1 to 4% methanol in EtOAc) and gave the title compound as an yellow oil. 13C-NMR (DMSO-d6) δ 165.3, 150.4, 150.0, 149.8, 149.3, 137.8, 122.2, 120.5, 118.8, 117.9, 114.0, 71.8, 55.7, 48.3, 18.6.

后处理

  1. customat 50-60° C
  2. additionwas added
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe mixture was extracted several times with EtOAc
  5. washthe combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe remaining material was purified by column chromatography on silica gel (elution with 1 to 4% methanol in EtOAc)

来源与证据

ORD记录
ord-4a54bf290030467893716d7e6663d365
来源数据集
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08034811B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记