Sodium hydride → 4-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)(4-methoxybenzyl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 1430933ノート

反応式

HRID 1430933 の反応式
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][C:4]([NH:8][C:9]2[C:14]3=[N:15][CH:16]=[C:17]([C:18]#[N:19])[N:13]3[N:12]=[C:11]([S:20][CH3:21])[N:10]=2)=[N:3]1.[H-].[Na+].Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1>CN(C=O)C>[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][C:4]([N:8]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:9]2[C:14]3=[N:15][CH:16]=[C:17]([C:18]#[N:19])[N:13]3[N:12]=[C:11]([S:20][CH3:21])[N:10]=2)=[N:3]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 867086354-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

生成物 1

HCID 867086364-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)(4-methoxybenzyl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile収率 84.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (157 mg, 0.521 mmol) was taken up in DMF (6 mL) under argon and NaH (22.92 mg, 0.573 mmol) was added. The reaction mixture was stirred at rt for 30 min, then alpha-chloro-4-methoxytoluene (0.074 mL, 0.547 mmol) was added. The reaction mixture was heated at 80° C. for 3 h. The reaction was quenched with sat'd NaHCO3 solution and extracted 3× with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to give 4-((1,5-dimethyl-1H-1,2,4-triazol-3-yl)(4-methoxybenzyl)amino)-2-(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (185 mg) as a red solid.

後処理

  1. temperatureThe reaction mixture was heated at 80° C. for 3 h
  2. customThe reaction was quenched with sat'd NaHCO3 solution
  3. extractionextracted 3× with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8995d874a0ce436c8f434fe81d48fcf2
出典データセット
uspto-grants-2015_01
特許番号
US08940736B2

反応ノート

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