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

HRID 329615Notes

Reaction equation

HRID 329615 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]1

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0% 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

  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

Sources & evidence

ORD record
ord-f202c4bbaff2494890f9c06aed5e6fab
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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