氢氧化钠 → N-(2-(二乙基氨基)乙基)-5-甲酰基-2,4-二甲基-1H-吡咯-3-甲酰胺

HRID 50004笔记

反应方程式

HRID 50004 反应方程式
[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=O)[C:4]=1[CH3:12])=[O:2].O[C:14]1C2N=NNC=2C=C[CH:15]=1.C([NH:25][CH2:26][CH2:27][NH:28][CH2:29][CH3:30])C.[OH-].[Na+]>O.[Cl-].[Na+].O.C(=O)(O)[O-].[Na+].C(N(CC)CC)C.CN(C)C=O>[CH2:14]([N:28]([CH2:29][CH3:30])[CH2:27][CH2:26][NH:25][C:9]([C:5]1[C:4]([CH3:12])=[C:3]([CH:1]=[O:2])[NH:7][C:6]=1[CH3:8])=[O:11])[CH3:15]

参与物

10

反应物 4

HCID 14798氢氧化钠HCID 67105N N'-二乙基乙二胺HCID 110737922,4-二甲基-5-醛基-1H-吡咯-3-羧酸HCID 178418300HCID 178418300，化合物

产物 1

HCID 20761785N-(2-(二乙基氨基)乙基)-5-甲酰基-2,4-二甲基-1H-吡咯-3-甲酰胺收率 43%

试剂、催化剂与溶剂 5

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8471三乙胺溶剂HCID 516892碳酸氢钠溶剂HCID 57417360Sodium chloride; water溶剂

实验过程

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 3000 mL of water, 2000 mL of brine and 3000 mL of saturated sodium bicarbonate solution and the pH adjusted to greater than 10 with 10 N sodium hydroxide. The mixture was extracted twice with 5000 mL each time of 10% methanol in dichloromethane and the extracts combined, dried over anhydrous magnesium sulfate and rotary evaporated to dryness. The mixture was with diluted with 1950 mL of toluene and rotary evaporated again to dryness. The residue was triturated with 3:1 hexane:diethyl ether (4000 mL). The solids were collected by vacuum filtration, washed twice with 400 mL of ethyl acetate and dried under vacuum at 34° C. for 21 hours to give 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (819 g, 43% yield) as a light brown solid. 1H-NMR (dimethylsulfoxide-d6) δ0.96 (t, 6H, 2×CH3), 2.31, 2.38 (2×s, 2×CH3), 2.51 (m, 6H 3×CH2), 3.28 (m, 2H, CH2), 7.34 (m, 1H, amide NH), 9.56 (s, 1H, CHO), 11.86 (s, 1H, pyrrole NH). MS m/z 266 [M+1].

后处理

  1. additionwere added
  2. extractionThe mixture was extracted twice with 5000 mL each time of 10% methanol in dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customrotary evaporated to dryness
  5. additionwith diluted with 1950 mL of toluene
  6. customrotary evaporated again to dryness
  7. customThe residue was triturated with 3:1 hexane
  8. filtrationThe solids were collected by vacuum filtration
  9. washwashed twice with 400 mL of ethyl acetate
  10. customdried under vacuum at 34° C. for 21 hours

来源与证据

ORD记录
ord-4280e8a1072d4ca989f211bca84eef5e
来源数据集
uspto-grants-2004_03
专利号
US06710067B2

反应笔记

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