Reaction equation
[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]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- stirringThis mixture was stirred overnight
- extractionextracted with 150 ml portions of dichloromethane
- customdried
- customevaporated
- customThe residue was chromatographed on a silica gel column
- washeluting with dichloromethane:methanol (95:5)
- customevaporated
- customthe solid recrystallized from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-00e6fd8afc264fa9b7c3d21e8d2a4baf
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04654343
Linked notes
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