Water → N-[3-(3-Methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]-N-2-propenylacetamide

HRID 35613

반응식

HRID 35613 반응식
[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](Br)[CH:24]=[CH2:25].O>CN(C)C=O>[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:12]=[C:13]([N:17]([CH2:25][CH:24]=[CH2:23])[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

참가 물질

6

반응물 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 7532415N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)acetamide

생성물 1

HCID 15595651N-[3-(3-Methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]-N-2-propenylacetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 3.0 g of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide in 250 ml of dimethylformamide under argon, was added 0.6 g of sodium hydride (50% in oil). This mixture was stirred for 1 hour, then 1.07 ml of allyl bromide was added. The mixture was stirred overnight, then poured into 200 ml of water and extracted with 150 ml portions of dichloromethane. The extracts were combined, dried and evaporated in vacuo. The residue was chromatographed as described in Example 1. The active fractions were combined, evaporated and the solid recrystallized from ethyl acetate-hexane, giving 1.46 g of the desired product as tan crystals, mp 114°-115° C.

후처리

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with 150 ml portions of dichloromethane
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed
  6. customevaporated
  7. customthe solid recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-0036a144edc24a78be11643491bf48cf
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767765

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