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

HRID 1906783

반응식

HRID 1906783 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+].CN(C)C=O.Br[CH2:29][CH:30]1[CH2:32][CH2:31]1>O>[CH:30]1([CH2:29][N:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]4[N:6]([C:2]([CH3:1])=[N:3][N:4]=4)[N:7]=3)[CH:12]=2)[C:18](=[O:20])[CH3:19])[CH2:32][CH2:31]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 7532415N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)acetamide

생성물 1

HCID 15595652N-(Cyclopropylmethyl)-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 3.0 g of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide, 0.6 g of sodium hydride (50% in oil) and 250 ml of dimethylformamide was stirred under argon for 1 hour, then 1.2 ml of (bromomethyl)cyclopropane was added. This 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. The residue was chromatographed on a silica gel column, eluting with dichloromethane:methanol (95:5). The active fractions were combined, evaporated and the solid recrystallized from ethyl acetate-hexane, giving 1.5 g of the desired product as pink crystals, mp 118°-121° C.

후처리

  1. stirringThis mixture was stirred overnight
  2. extractionextracted with 150 ml portions of dichloromethane
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with dichloromethane:methanol (95:5)
  7. customevaporated
  8. customthe solid recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-00e6fd8afc264fa9b7c3d21e8d2a4baf
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04654343

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