Sodium Hydroxide → N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

HRID 1008199

反応式

HRID 1008199 の反応式
[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]

参加物

10

反応物 4

HCID 14798Sodium HydroxideHCID 67105N,N'-DiethylethylenediamineHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic AcidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 20761785N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide収率 43%

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 516892Sodium Bicarbonate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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) δ 0.96 (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].

後処理

  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

出典と根拠

ORDレコード
ord-ade2bd5e3d844ff99b918fd1a6856274
出典データセット
uspto-grants-2004_09
特許番号
US06797725B2

関連ノート

読み込み中…