Ethyl isocyanate → 7-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

HRID 2112931ノート

反応式

HRID 2112931 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH2:15])[N:14]=[C:10]2[CH:9]=[C:8]([Br:16])[CH:7]=1)=[O:5])[CH3:2].[CH2:17]([N:19]=[C:20]=[O:21])[CH3:18]>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:20]([NH:19][CH2:17][CH3:18])=[O:21])[N:14]=[C:10]2[CH:9]=[C:8]([Br:16])[CH:7]=1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 8022Ethyl isocyanateHCID 576430722-Amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

生成物 1

HCID 576430687-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 22635083Tetrahydrofuran toluene溶媒

反応条件

温度
100 °C

実験手順

2-Amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (7) (760 mg, 2.66 mmol) was dissolved in THF/toluene (1:1, 40 mL), then ethyl isocyanate (1.89 g, 26.6 mmol) and a catalytic quantity of dibutyltindiacetate (10 drops) were added to the mixture. The reaction was then heated in a sealed tube at 100° C. for 15 h. This mixture was allowed to cool, then the solvents removed under reduced pressure to afford a solid which was purified by flash chromatography on silica 2% MeOH/CH2Cl2 as eluant) to give 7-bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (8) LCMS (APCI+) 356, 358.

後処理

  1. temperatureto cool
  2. customthe solvents removed under reduced pressure
  3. customto afford a solid which
  4. customwas purified by flash chromatography on silica 2% MeOH/CH2Cl2 as eluant)

出典と根拠

ORDレコード
ord-6be9ee39dfdb43d5899d1b9780a1d2e0
出典データセット
uspto-grants-2009_04
特許番号
US07524860B2

反応ノート

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