6-Amino-3-chloropyridazine → HCID 178463304, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.CO[C:11](OC)([N:13]([CH3:15])[CH3:14])[CH3:12].COC1CCCC1>>[Cl:1][C:2]1[N:7]=[N:6][C:5](/[N:8]=[C:11](/[N:13]([CH3:15])[CH3:14])\[CH3:12])=[CH:4][CH:3]=1Participants
4
Procedure
Combine 6-chloropyridazin-3-amine (1.500 kg, 11.58 mol); 1,1-dimethoxy-N,N-dimethylethanamine (2.313 kg, 17.37 mol) and cyclopentyl methyl ether (8.25 L) then heat to 98° C. while distilling off the resulting methanol byproduct. After 4 h, the reaction mixture is cooled to ambient temperature and heptanes (11.2 L) is added to the reaction solution for crystallizing the product. The title compound is collected by filtration and is dried. (1.494 kg, 64.95%; mp=73° C.)
Workup
- distillationwhile distilling off the resulting methanol byproduct
- additionheptanes (11.2 L) is added to the reaction solution
- customfor crystallizing the product
- filtrationThe title compound is collected by filtration
- customis dried
Sources & evidence
- ORD record
- ord-cc25a493e9be43f5bf9b19c923cba491
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897600B2
Reaction notes
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