Sodium Iodide → Ethyl 6-(aminocarbonyl)-8-(2-ethyl-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 427507ノート

反応式

HRID 427507 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([C:8]([NH2:10])=[O:9])[CH:7]=1.[CH2:20]([C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl)[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(Cl)Cl.CC(C)=O>[NH2:10][C:8]([C:6]1[CH:7]=[C:2]([NH:1][CH2:24][C:23]2[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:22]=2[CH2:20][CH3:21])[C:3]2[N:4]([C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:12]([CH3:14])[N:13]=2)[CH:5]=1)=[O:9]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 18357447Ethyl 8-amino-6-(aminocarbonyl)-2-methylimidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 18357437Ethyl 6-(aminocarbonyl)-8-(2-ethyl-6-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine-3-carboxylate収率 56%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

実験手順

Ethyl 8-amino-6-(aminocarbonyl)-2-methylimidazo[1,2-a]pyridine-3-carboxylate (0.41 g, 1.6 mmol), 2-ethyl-6-methylbenzylchloride, sodium carbonate (0.7 g, 6.6 mmol), sodium iodide (0.15 g, 1.0 mmol) and acetone (20 ml) were refluxed for 44 h. Methylene chloride was added and the solids were removed by filtration. The filtrate was evaporated under reduced pressure and purification of the residue by column chromatography on silica gel eluting with methylene chloride:methanol (100:4) gave 0.35 g (56%) of the title compound. 1H-NMR (300 MHz, CDCl3): δ1.25 (t, 3H), 1.45 (t, 3H), 2.35 (s, 3H), 3.65 (s, 3H), 2.7 (q, 2H), 4.4-4.45 (m, 4H), 5.0 (t, 1H), 6.95 (s, 1H), 7.0-7.2 (m, 3H), 9.2 (s, 1H)

後処理

  1. customthe solids were removed by filtration
  2. customThe filtrate was evaporated under reduced pressure and purification of the residue by column chromatography on silica gel eluting with methylene chloride:methanol (100:4)

出典と根拠

ORDレコード
ord-73816c7bdc1842d68dbc85de90bfe61c
出典データセット
uspto-grants-2001_11
特許番号
US06313137B1

反応ノート

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