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

HRID 427507노트

반응식

HRID 427507 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-73816c7bdc1842d68dbc85de90bfe61c
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313137B1

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