3,6-Dichloropyridazine → (6-Iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amine

HRID 548873Notes

Reaction equation

HRID 548873 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1NC.Cl[C:16]1[N:17]=[N:18][C:19]([I:22])=[CH:20][CH:21]=1.Cl[C:24]1[N:25]=NC(Cl)=CC=1>>[I:22][C:19]1[N:18]=[N:17][C:16]([NH:25][CH2:24][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 673313,6-DichloropyridazineHCID 154188393-Chloro-6-iodopyridazineHCID 59594513(5-Methyl-3-phenyl-4-isoxazolyl)-methylamine

Product 1

HCID 86630896(6-Iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amineYield 24%

Procedure

As described for example 72, (5-methyl-3-phenyl-isoxazol-4-yl)-methylamine (2.0 g, 10.6 mmol) was converted using 3-chloro-6-iodopyridazine (Goodman, A. J.; Stanforth, S. P.; Tarbit, B. Tetrahedron 1999, 55, 15067) instead of 3,6-dichloropyridazine to the title compound (1.0 g, 24%) which was contaminated with ca. 33% of (6-chloro-pyridazin-3-yl)-(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amine (example 72). The product was obtained as a white solid. MS: m/e=393.0 [M+H]+.

Sources & evidence

ORD record
ord-22fe2c14ea31423dbc913dbb3f007ff1
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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