Water → N-Ethyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide

HRID 329610

反応式

HRID 329610 の反応式
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[H-].[Na+].[CH2:23](I)[CH3:24].O>CN(C)C=O>[CH2:23]([N:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[N:7]=2)[CH:12]=1)[C:18](=[O:20])[CH3:19])[CH3:24]

参加物

6

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 7532415N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)acetamide

生成物 1

HCID 15595648N-Ethyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 12.5 g of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl]phenyl]acetamide (U.S. Pat. No. 4,112,095) in 500 ml of dimethylformamide under argon, was added 2.47 g of sodium hydride (50% in oil). The mixture was stirred for one hour, then 4.1 ml of ethyl iodide was added. This mixture was stirred for 2.5 days, then poured into 1.5 liters of water and extracted with 150 ml portions of dichloromethane. The extracts were combined, dried and evaporated in vacuo. The residue was chromatographed on a Waters Prep 500 silica gel column, eluting with dichloromethane:methanol (97:3). Fractions 8-13 were combined, evaporated in vacuo and the solid recrystallized from dichloromethane-hexane, giving 6.54 g of the desired product, mp 180°-185° C.

後処理

  1. stirringThis mixture was stirred for 2.5 days
  2. extractionextracted with 150 ml portions of dichloromethane
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on a Waters Prep 500 silica gel column
  6. washeluting with dichloromethane:methanol (97:3)
  7. customevaporated in vacuo
  8. customthe solid recrystallized from dichloromethane-hexane

出典と根拠

ORDレコード
ord-f7c4f718e0764902a9ffdcd234948e35
出典データセット
uspto-grants-1990_01
特許番号
US04892873

関連ノート

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