Hydrogen Sulfide → t-Butyl 4-(5-thiocarbamoylfuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

HRID 1291028ノート

反応式

HRID 1291028 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH:14][C:15]3[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:16]=3)=[O:13])[O:9][C:6]2=[N:7][CH:8]=1)#[N:2].[SH2:30]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH:14][C:15]3[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[CH:17][CH:16]=3)=[O:13])[O:9][C:6]2=[N:7][CH:8]=1)(=[S:30])[NH2:2]

参加物

5

反応物 2

HCID 402Hydrogen SulfideHCID 10500772t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

生成物 1

HCID 10622396t-Butyl 4-(5-thiocarbamoylfuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8471Triethylamine溶媒

実験手順

t-Butyl 4-(5-cyanofuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate (430 mg, 1.10 mmol) was dissolved in a mixed solvent of pyridine (16 ml) and triethylamine (4 ml), and a hydrogen sulfide gas was blown in for 10 minutes. The mixture was stirred at room temperature for 18 hours. The solvent was distilled away from the reaction mixture under reduced pressure to give t-butyl 4-(5-thiocarbamoylfuro[2,3-b]pyridine-2-carbonylamino)phenoxyacetate as a yellow solid. This solid was dissolved in acetone (15 ml) and methyl iodide (1.0 ml) was added, which was followed by refluxing under heating for 1.5 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure to give t-butyl 4-[5-[(1-methylthio)iminomethyl]furo[2,3-b]pyridine-2-carbonylamino]phenoxyacetate as a yellow solid. Methanol (15 ml) and ammonium acetate (150 mg, 1.95 mmol) were added and the mixture was refluxed under heating for 2 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure and the residue was purified by silica gel (Chromatorex, NH type, Fuji Silysia Chemical) column chromatography (chloroform/methanol=5/1) to give 35 mg of compound (238) as a yellow solid (11% in 3 steps).

後処理

  1. customwas blown in for 10 minutes
  2. distillationThe solvent was distilled away from the reaction mixture under reduced pressure

出典と根拠

ORDレコード
ord-2c20d3f96340441da664bc244e044d3a
出典データセット
uspto-grants-1998_05
特許番号
US05753670

反応ノート

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