聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → Tert-butyl 3-((3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl)azetidine-1-carboxylate

HRID 405802

反应方程式

HRID 405802 反应方程式
C(C1NC=CN=1)(C1NC=CN=1)=O.[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([CH2:24][C:25]([OH:27])=O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].O[N:29]=[C:30]([C:32]1[CH:33]=[CH:34][C:35]([CH3:50])=[C:36]([NH:38][C:39]([C:41]2[N:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]3=[N:43][CH:42]=2)=[O:40])[CH:37]=1)[NH2:31].O>CN1C(=O)CCC1>[N:43]1[CH:42]=[C:41]([C:39]([NH:38][C:36]2[CH:37]=[C:32]([C:30]3[N:29]=[C:25]([CH2:24][CH:22]4[CH2:21][N:20]([C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[CH2:23]4)[O:27][N:31]=3)[CH:33]=[CH:34][C:35]=2[CH3:50])=[O:40])[N:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=12

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 110959891-(叔丁氧基羰基)氮杂环丁烷-3-乙酸HCID 86677441N-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

产物 1

HCID 71281398Tert-butyl 3-((3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl)azetidine-1-carboxylate

试剂、催化剂与溶剂 1

HCID 13387N-甲基吡咯烷酮溶剂

反应条件

温度
125 °C

实验过程

Carbonyl diimidazole (CDI) (52.0 mg, 0.32 mmol) was added to a stirred solution of 2-(1-(tert-butoxycarbonyl)azetidin-3-yl)acetic acid (69.0 mg, 0.32 mmol) in NMP (1.0 mL). After 20 minutes, N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (49.5 mg, 0.16 mmol) was added in one portion and the resulting solution was stirred for 30 minutes before it was heated at 125° C. for 15 minutes in a microwave reactor. The reaction mixture was added dropwise to water (20 mL) with stirring. The precipitate was filtered and dried to give tert-butyl 3-((3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl)azetidine-1-carboxylate (54). MS m/z 489.2 (M+1)+.

后处理

  1. stirringwith stirring
  2. filtrationThe precipitate was filtered
  3. customdried

来源与证据

ORD记录
ord-6cdf3e92c7e2492dab844346282e1328
来源数据集
uspto-grants-2014_06
专利号
US08754071B2

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